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

HRID 1891031Notes

Reaction equation

HRID 1891031 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

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 112431895,6-Diphenylfuro[2,3-d]pyrimidin-4-ol

Product 1

HCID 114496374-Chloro-5,6-diphenylfuro[2,3-d]pyrimidineYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 the title compound as a white solid (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

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

Sources & evidence

ORD record
ord-84fd87a46ac04178b2d7af5353a187b7
Source dataset
uspto-grants-2013_08
Patent number
US08507502B2

Reaction notes

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