1-PHENYLPYRIMIDIN-2(1H)-ONE → HCID 58016539, compound

HRID 2200761Notes

Reaction equation

HRID 2200761 reaction equation
[C:1]1([N:7]2[CH:12]=[CH:11][CH:10]=[N:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C1COCC1.CO>[C:1]1([N:7]2[CH:12]=[CH:11][CH2:10][NH:9][C:8]2=[O:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 28184611-PHENYLPYRIMIDIN-2(1H)-ONEHCID 4311764Sodium borohydride

Product 1

HCID 58016539HCID 58016539, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-phenylpyrimidin-2(1H)-one (250 mg, 1.45 mmol) in dry THF (20 mL) was added a solution of NaBH4 (58 mg, 1.5 mmol) in 20 mL MeOH by dropwise at 0° C. The reaction mixture was stirred at rt for 1 h. The mixture was concentrated to remove DCM, the residue was purified by SFC to give 1-phenyl-3,4-dihydropyrimidin-2(1H)-one and Compound 365 (74.8 mg, 30% yield) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.41-7.33 (m, 4H), 7.23-7.21 (m, 1H), 6.53 (brs, 1H), 6.14-6.11 (m, 1H), 4.88-4.84 (m, 1H), 4.32-4.31 (m, 2H). MS (ESI) m/z [M+H]+ 174.9.

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove DCM
  3. customthe residue was purified by SFC

Sources & evidence

ORD record
ord-c81970a76160471ba74b363e2ea03d76
Source dataset
uspto-grants-2016_06
Patent number
US09359379B2

Reaction notes

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