Phosphorus oxychloride → 4-Chloro-5,6-diphenylfuro[2,3-d]pyrimidine

HRID 1095470Notes

Reaction equation

[C:1]1([C:7]2[C:15]3[C:14](=O)[NH:13][CH:12]=[N:11][C:10]=3[O:9][C:8]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:25].C(=O)(O)[O-].[Na+]>O>[Cl:25][C:14]1[C:15]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:9][C:10]=2[N:11]=[CH:12][N:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5,6-diphenylfuro[2,3-d]pyrimidin-4(3H)-one (3 g) and POCl3 (30 mL) was heated at 55-65° C. for 3 h. Water was then added followed by sodium bicarbonate. The resulting mixture was extracted with ethyl acetate. The organic layer was concentrated and the crude compound was purified by silica gel column chromatography using a mixture of hexanes:ethyl acetate (95:5), to give white solid 4-chloro-5,6-diphenylfuro[2,3-d]pyrimidine (2 g, 63%). 1H NMR (300 MHz, CDCl3): δ 8.77 (s, 1H), 7.61-7.58 (m, 2H), 7.52-7.46 (m, 5H), 7.35-7.32 (m, 3H). LC-MS (ESI) m/z 307.0 (M+H).

Workup

extractionThe resulting mixture was extracted with ethyl acetate
concentrationThe organic layer was concentrated
customthe crude compound was purified by silica gel column chromatography
additiona mixture of hexanes:ethyl acetate (95:5)

Sources & evidence

ORD record: ord-29733963437f48c6ab86acc004933e69
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138194B2

Reaction notes

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