Imidazole → (R)-6-(3-((tert-Butyldimethylsilyl)oxy)-2-hydroxypropyl)-5-(3-chlorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 624563Notes

Reaction equation

HRID 624563 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([CH2:21][C@@H:22]([OH:25])[CH2:23][OH:24])[CH:10]=[C:11]3[C:16]=2[C:15](=[O:17])[N:14]([CH3:18])[C:13](=[O:19])[N:12]3[CH3:20])[CH:5]=[CH:6][CH:7]=1.[C:26]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])([CH3:28])[CH3:27].N1C=CN=C1>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O>[Si:30]([O:24][CH2:23][C@H:22]([OH:25])[CH2:21][N:9]1[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[C:16]2[C:11]([N:12]([CH3:20])[C:13](=[O:19])[N:14]([CH3:18])[C:15]2=[O:17])=[CH:10]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:32])[CH3:31]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride2×HCID 86722886(R)-5-(3-Chlorophenyl)-6-(2,3-dihydroxypropyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 86722888(R)-6-(3-((tert-Butyldimethylsilyl)oxy)-2-hydroxypropyl)-5-(3-chlorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-5-(3-chlorophenyl)-6-(2,3-dihydroxypropyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (1.39 g, 3.8 mmol), tert-butylchlorodimethylsilane (633 mg, 4.2 mmol), imidazole (520 mg, 7.6 mmol) and DMAP (47 mg, 0.38 mmol) in DMF (14 mL) was stirred at room temperature for 2 hours. A further portion of tert-butylchlorodimethylsilane (172 mg, 1.1 mmol) was added and the mixture stirred for a further 1 hour. The reaction mixture was diluted with EtOAc (70 mL) and washed with 0.5M HCl (3×35 mL) and brine (1×35 mL). The organic phase was dried over magnesium sulfate and evaporated under vacuum. Trituration with hexane afforded the title compound.

Workup

  1. washwashed with 0.5M HCl (3×35 mL) and brine (1×35 mL)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-349c671a0a164fab8f2822f5cda56ea5
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

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