Water → HCID 86723474, compound

HRID 2201239Notes

Reaction equation

HRID 2201239 reaction equation
[CH3:1][N:2]1[C:7]2=[CH:8][NH:9][C:10]([C:11]3[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=3)=[C:6]2[C:5](=[O:17])[N:4]([CH3:18])[C:3]1=[O:19].Br[CH2:21][CH2:22][CH2:23][C:24]([N:26]([O:28][CH3:29])[CH3:27])=[O:25].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([CH2:21][CH2:22][CH2:23][C:24]([N:26]([O:28][CH3:29])[CH3:27])=[O:25])[C:10]([C:11]3[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=3)=[C:6]2[C:5](=[O:17])[N:4]([CH3:18])[C:3]1=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 14642623130250-57-62×HCID 1363484071,3-Dimethyl-5-(1-methyl-1H-pyrazol-3-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 86723474HCID 86723474, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,3-Dimethyl-5-(1-methyl-1H-pyrazol-3-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (800 mg, 3.09 mmol), 4-bromo-N-methoxy-N-methylbutanamide (Intermediate P) (843 mg, 4.01 mmol) and cesium carbonate (2011 mg, 6.17 mmol) were suspended in DMF (11.100 ml) and the mixture was stirred at room temperature for 22 hours. The mixture was poured into water (50 ml) and extracted with DCM (3×100 ml). The combined organic extracts were washed with water (2×50 ml) and brine (50 ml), dried over sodium sulfate and evaporated under vacuum. Purification by mass-directed HPLC under the following conditions afforded the title compound.

Workup

  1. extractionextracted with DCM (3×100 ml)
  2. washThe combined organic extracts were washed with water (2×50 ml) and brine (50 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated under vacuum
  5. customPurification by mass-directed HPLC under the following conditions

Sources & evidence

ORD record
ord-514708b0248943feaf8185d1a94909ed
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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