Sodium borohydride → 5-(3-fluorophenyl)-10-hydroxy-1,3-dimethyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione

HRID 2201302Notes

Reaction equation

HRID 2201302 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([C:12](=[O:17])[CH2:13][CH2:14][CH2:15]3)=[C:10]3[N:18]([CH3:25])[C:19](=[O:24])[N:20]([CH3:23])[C:21](=[O:22])[C:9]=23)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([CH:12]([OH:17])[CH2:13][CH2:14][CH2:15]3)=[C:10]3[N:18]([CH3:25])[C:19](=[O:24])[N:20]([CH3:23])[C:21](=[O:22])[C:9]=23)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 867235335-(3-Fluorophenyl)-1,3-dimethyl-8,9-dihydropyrimido[4,5-a]indolizine-2,4,10(1H,3H,7H)-trione

Product 1

HCID 867234235-(3-fluorophenyl)-10-hydroxy-1,3-dimethyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 5-(3-fluorophenyl)-1,3-dimethyl-8,9-dihydropyrimido[4,5-a]indolizine-2,4,10(1H,3H,7H)-trione (step 1)(150 mg, 0.439 mmol) in MeOH (2197 μL) at 0° C. was added sodium borohydride (49.9 mg, 1.318 mmol) portionwise. The resulting yellow solution was warmed to room temperature and stirred for 15 minutes. The reaction was concentrated in vacuo. The residue was diluted with water (5 mL) and DCM (10 mL). The aqueous phase was separated and extracted with DCM (3×10 mL). The combined organic fractions were dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as a pale yellow solid;

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionThe residue was diluted with water (5 mL) and DCM (10 mL)
  3. customThe aqueous phase was separated
  4. extractionextracted with DCM (3×10 mL)
  5. dry with materialThe combined organic fractions were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7d35bd3232cd4c6eb04dd308ee17be40
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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