3,3'-(1,4-Phenyl-ene)bis-[2-(propyl-amino)-benzofuro[3,2-d]pyrimidin-4(3H)-one] ethanol disolvate.

The title compound, C(32)H(28)N(6)O(4)·2C(2)H(5)OH, consists of two 2-(propyl-amino)-benzofuro[3,2-d]pyrimidin-4(3H)-one units connected, via one of the pyrimidine N atoms, to a bridging benzene ring in the 1,4 positions. Two ethanol solvent mol-ecules are also present. The main mol-ecule lies on a center of symmetry located at the center of the benzene ring. The fused-ring system of the benzofuro[3,2-d]pyrimidine moiety is nearly planar (r.m.s. deviation = 0.016 Å) and forms a dihedral angle of 78.21 (7)° with the central benzene ring. The crystal structure features O-H⋯O and N-H⋯O inter-actions. The C atoms of the propyl-amino side chain in the main mol-ecule and the ethyl group in the solvent mol-ecule are disordered over two positions, with site-occupancy factors 0.34:0.66 and 0.42:0.58, respectively.

Ethyl 2-diethyl-amino-4-oxo-3,5-diphenyl-4,5-dihydro-3H-pyrrolo-[3,2-d]pyrimidine-7-carboxyl-ate.

In the title compound, C(25)H(26)N(4)O(3), the two fused pyrrolo-[3,2-d]pyrimidine rings form a dihedral angle of 3.7 (2)°. The two substituent phenyl rings are twisted with respect to the pyrrole and pyrimidine rings, making dihedral angles of 57.2 (2) and 69.0 (2)°, respectively. The ethyl and eth-oxy groups are disordered over two positions; the site occupancies are 0.53 (1) and 0.47 (1) for ethyl, and 0.63 (1) and 0.37 (1) for eth-oxy. The crystal packing features C-H⋯O hydrogen bonds.

Efficient synthesis and biological evaluation of some 2,4-diamino-furo[2,3-d]pyrimidine derivatives.

The carbodiimides 2, obtained from aza-Wittig reactions of iminophosphorane 1 with aromatic isocyanates, reacted with ammonia to give ethyl 3,4-dihydro-6-methyl-4-oxo-2-arylamino-furo[2,3-d]pyrimidine-5-carboxylate 3. Further reaction of 3 with POCl(3) and various amines generated ethyl 4-alkylamino-2-arylamino-6-methyl-furo[2,3-d]pyrimidine-5-carboxylate 5 in good yields. Their structures were confirmed by (1)H NMR, EI-Ms, IR and elemental analysis. Compound 5b was further analyzed by single crystal X-ray diffraction. Compound 5 exhibited cytotoxicity against two lung cancer cell lines. For example, compound 5a showed the best inhibition activities against A459 with IC(50) 0.8µM.

3-(4-Fluoro-phen-yl)-2-(2-naphth-yloxy)-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile.

The title compound, C(29)H(17)FN(4)O(2), may be used as a new precursor for obtaining bioactive mol-ecules. There are two crystallographically independent mol-ecules in the asymmetric unit. The phenyl ring, 4-fluoro-phenyl ring and 2-naphth-yloxy ring are twisted with respect to the pyrrolopyrimidine ring by 52.30 (11)/49.05 (11), 80.94 (10)/88.36 (10) and 60.58 (7)/83.76 (7)°, respectively. The crystal packing is stabilized by weak C-H⋯N hydrogen bonds.

A facile synthesis and fungicidal activities of 2-(alkylamino)-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-ones.

The aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates generated carbodiimides 4, which were reacted with alkylamines under mild conditions to give a series of 2-(alkylamino)-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-ones 6 and 8 in satisfactory yield. Their structures were confirmed by (1)H NMR, EI-MS, IR and elementary analysis, and compound 8c was further analyzed by single-crystal X-ray diffraction. The preliminary bioassays indicated that these compounds showed excellent fungicidal activities against six kinds of fungi.

2-(Dibutyl-amino)-3-(4-fluoro-phen-yl)-5,6,7,8-tetra-hydro-7-methyl-6,8-di-phenyl-pyridine-[3',4':2,3]thieno[5,4-d]pyrimidin-4(3H)-one.

In the crystal structure of the title compound, C(36)H(39)FN(4)OS, the two fused rings of the thienopyrimidine system are coplanar. The 4-fluoro-phenyl ring is twisted with respect to the heterocyclic pyrimidinone ring by 67.21 (14)°. The piperidine ring shows a half-chair conformation. One of the n-butyl chains is disordered equally over two sites. The crystal packing is stabilized by C-H⋯O hydrogen bonds.

3-Phenyl-2-(prop-2-yn-yloxy)-1-benzofuro[3,2-d]pyrimidin-4(3H)-one.

In the title compound, C(19)H(12)N(2)O(3), the 1-benzofuro[3,2-d]pyrimidinone unit is approximately planar, the maximum deviation from the mean plane being 0.045 (1) Å. The attached phenyl ring makes a dihedral angle of 86.73 (6)° with the fused ring system. The packing of the mol-ecules in the crystal structure is mainly governed by C-H⋯π hydrogen-bonding inter-actions.

Ethyl 3-(4-fluoro-phen-yl)-6-methyl-4-oxo-2-(1-cyclohexylamino)-3,4-dihydro-furo[2,3-d]pyrimidine-5-carboxyl-ate.

In the crystal structure of the title compound, C(22)H(24)FN(3)O(4), the two fused rings of furo[2,3-d]pyrimidine form a dihedral angle of 0.88 (13)°. The attached benzene ring is twisted with respect to the heterocyclic pyrimidinone ring, making a dihedral angle of 75.07 (12)°. The cyclo-hexyl ring shows a distorted chair conformation. The mol-ecular structure is stabilized by intra-molecular C-H⋯O and C-H⋯N hydrogen-bonding inter-actions. The crystal packing is mainly stabilized by C-H⋯π hydrogen-bond inter-actions. Further stability is provided by C-F⋯π and C-O⋯π stacking inter-actions.

Ethyl 2-[1-(4-chloro-phen-yl)-2,5-dioxo-1,2,3,5-tetra-hydro-imidazo[1',2':1,2]pyrimidino[5,4-b][1]benzofuran-3-yl]acetate.

The asymmetric unit of the title compound, C(22)H(16)ClN(3)O(5), consists of two crystallographically independent mol-ecules. The fused rings of the imidazo[1,2-a]benzo[4,5]furo[3,2-d]pyrimidine system are nearly coplanar and the chlorophenyl rings are twisted with respect to the two pyrimidinone ring systems by 71.00 (2) and 62.59 (2)°. The C atoms of the ethyl side chain are disordered and were refined using a split model. In the crystal structure, the mol-ecules are connected via weak intra- and inter-molecular C-H⋯O inter-actions are present. The ethyl group in one molecule is disordered over two positions, with site occupancy factors 0.55 and 0.45; in the other molecule only the methyl group is disordered over two positions, with site occupancy factors 0.6 and 0.4.