Phosphorus oxychloride → 7-Chloro-2-(4-fluorophenyl)-oxazolo[5,4-d]pyrimidine

HRID 718266Notes

Reaction equation

HRID 718266 reaction equation
O[C:2]1[C:7]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:6](O)[N:5]=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.O=P(Cl)(Cl)[Cl:30]>>[Cl:30][C:6]1[C:7]2[N:8]=[C:9]([C:10]3[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=3)[O:17][C:2]=2[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178522470HCID 178522470, compound

Product 1

HCID 866624407-Chloro-2-(4-fluorophenyl)-oxazolo[5,4-d]pyrimidineYield 30%

Conditions

Temperature
90 °C

Procedure

To a solution of N-(4,6-dihydroxypyrimidin-5-yl)-4-fluorobenzamide (0.30 g, 1.20 mmol) in POCl3 (6 ml) was added diisopropylethylamine (0.42 ml, 2.41 mmol). The reaction mixture was stirred under N2 at 90° C. for 3.5 hours. The reaction mixture was allowed to cool down to room temperature and the volatiles were evaporated to dryness. The residue was diluted with water and the aqueous phase was extracted with diethyl ether. The combined organic layers were washed with a saturated NaHCO3 solution and brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (CH2Cl2/MeOH 100:1) to yield the title compound as a white solid (0.13 g, 30%).

Workup

  1. temperatureto cool down to room temperature
  2. customthe volatiles were evaporated to dryness
  3. additionThe residue was diluted with water
  4. extractionthe aqueous phase was extracted with diethyl ether
  5. washThe combined organic layers were washed with a saturated NaHCO3 solution and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel (CH2Cl2/MeOH 100:1)

Sources & evidence

ORD record
ord-07835c52fcb74ea7a935973f6c00c282
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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