Sodium borohydride → HCID 86723467, compound

HRID 2201233Notes

Reaction equation

HRID 2201233 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:5]=[C:6]([C:9](=[O:33])[CH2:10][CH2:11][N:12]2[C:20]([C:21]3[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=3)[C:24]#[N:25])=[C:19]3[C:14]([N:15]([CH3:32])[C:16](=[O:31])[N:17]([CH3:30])[C:18]3=[O:29])=[CH:13]2)[S:7][CH:8]=1>CO>[Cl:3][C:4]1[N:5]=[C:6]([CH:9]([OH:33])[CH2:10][CH2:11][N:12]2[C:20]([C:21]3[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=3)[C:24]#[N:25])=[C:19]3[C:14]([N:15]([CH3:32])[C:16](=[O:31])[N:17]([CH3:30])[C:18]3=[O:29])=[CH:13]2)[S:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86723468HCID 86723468, compound

Product 1

HCID 86723467HCID 86723467, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (408 mg, 10.80 mmol) was added to a solution of 3-(6-(3-(4-chlorothiazol-2-yl)-3-oxopropyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (490 mg, 1.080 mmol) in methanol (20 mL). The mixture was stirred at room temp. for 25 mins, then quenched with saturated NaHCO3(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. customquenched with saturated NaHCO3(aq)
  2. extractionextracted with chloroform (3×)
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-f4561fb40f0d4b1dab2e84cb70782b07
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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