Sodium borohydride → 3-(6-(4-(4-Chlorothiazol-2-yl)-4-hydroxybutyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

HRID 2201214Notes

Reaction equation

[BH4-].[Na+].[Cl:3][C:4]1[N:5]=[C:6]([C:9](=[O:34])[CH2:10][CH2:11][CH2:12][N:13]2[C:21]([C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=3)[C:25]#[N:26])=[C:20]3[C:15]([N:16]([CH3:33])[C:17](=[O:32])[N:18]([CH3:31])[C:19]3=[O:30])=[CH:14]2)[S:7][CH:8]=1>C(O)C>[Cl:3][C:4]1[N:5]=[C:6]([CH:9]([OH:34])[CH2:10][CH2:11][CH2:12][N:13]2[C:21]([C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=3)[C:25]#[N:26])=[C:20]3[C:15]([N:16]([CH3:33])[C:17](=[O:32])[N:18]([CH3:31])[C:19]3=[O:30])=[CH:14]2)[S:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium borohydride (0.606 g, 16.03 mmol) was added portionwise to a suspension of 3-(6-(4-(4-chlorothiazol-2-yl)-4-oxobutyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (2.5 g, 5.34 mmol) in ethanol (53.4 mL) at 0° C. The reaction mixture was stirred for 15 minutes at 0° C., the quenched with water (25 mL) and extracted with DCM (3×50 mL). The combined organic fractions were dried over magnesium sulfate and evaporated under reduced pressure to afford the title compound.

Workup

customthe quenched with water (25 mL)
extractionextracted with DCM (3×50 mL)
dry with materialThe combined organic fractions were dried over magnesium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-cb5f337bcaa4468798ba3b00614be78d
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359381B2

Reaction notes

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