Sodium borohydride → 6-(3-(4-Chlorothiazol-2-yl)-3-hydroxypropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2201220Notes

Reaction equation

HRID 2201220 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:5]=[C:6]([C:9](=[O:31])[CH2:10][CH2:11][N:12]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:19]3[C:14]([N:15]([CH3:30])[C:16](=[O:29])[N:17]([CH3:28])[C:18]3=[O:27])=[CH:13]2)[S:7][CH:8]=1>CO>[Cl:3][C:4]1[N:5]=[C:6]([CH:9]([OH:31])[CH2:10][CH2:11][N:12]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:19]3[C:14]([N:15]([CH3:30])[C:16](=[O:29])[N:17]([CH3:28])[C:18]3=[O:27])=[CH:13]2)[S:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 867234576-(3-(4-Chlorothiazol-2-yl)-3-oxopropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 867234586-(3-(4-Chlorothiazol-2-yl)-3-hydroxypropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (415 mg, 10.96 mmol) was added to a suspension of 6-(3-(4-chlorothiazol-2-yl)-3-oxopropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (470 mg, 1.096 mmol) in methanol (20 mL). The mixture was stirred at room temperature for 15 mins. The reaction was quenched with saturated NH4Cl(aq) and extracted with chloroform (3×). The combined organic extracts were passed through a hydrophobic frit and evaporated under vacuum to afford the title compound.

Workup

  1. customThe reaction was quenched with saturated NH4Cl(aq)
  2. extractionextracted with chloroform (3×)
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-026c751460914672a606d507e8249e85
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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