Lithium Chloride → 7-(1-(4-Chlorothiazol-2-yl)-3-hydroxy-2,2-dimethylpropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2201236Notes

Reaction equation

HRID 2201236 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:5]=[C:6]([CH:9]([C:17]2[NH:18][C:19]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:20]3[C:25](=[O:26])[N:24]([CH3:27])[C:23](=[O:28])[N:22]([CH3:29])[C:21]=23)[C:10]([CH3:16])([CH3:15])[C:11](OC)=[O:12])[S:7][CH:8]=1.[Cl-].[Li+]>CO>[Cl:3][C:4]1[N:5]=[C:6]([CH:9]([C:17]2[NH:18][C:19]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[C:20]3[C:25](=[O:26])[N:24]([CH3:27])[C:23](=[O:28])[N:22]([CH3:29])[C:21]=23)[C:10]([CH3:16])([CH3:15])[CH2:11][OH:12])[S:7][CH:8]=1

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 86723469Methyl 3-(4-chlorothiazol-2-yl)-3-(1,3-dimethyl-2,4-dioxo-5-phenyl-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-7-yl)-2,2-dimethylpropanoate

Product 1

HCID 867234717-(1-(4-Chlorothiazol-2-yl)-3-hydroxy-2,2-dimethylpropyl)-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 (46.6 mg, 1.232 mmol) was added to a mixture of methyl 3-(4-chloro thiazol-2-yl)-3-(1,3-dimethyl-2,4-dioxo-5-phenyl-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-7-yl)-2,2-dimethylpropanoate (120 mg, 0.246 mmol) and lithium chloride (52.2 mg, 1.232 mmol) in methanol (10 mL). The mixture was stirred at room temp. for 30 mins. The reaction was quenched with saturated NaHCO3(aq) and extracted with DCM (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 NaHCO3(aq)
  2. extractionextracted with DCM (3×)
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-15c1a15359d84204b24ad4c799346e23
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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