Dimethylformamide → HCID 118022971, compound

HRID 2171814Notes

Reaction equation

HRID 2171814 reaction equation
[CH:1]1([C:7]2[S:25][C:10]3[N:11]=[C:12]([CH3:24])[N:13]=[C:14]([CH2:15][N:16]4[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]4[CH2:22][OH:23])[C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:26]N(C=O)C.[H-].[Na+].CI>O>[CH:1]1([C:7]2[S:25][C:10]3[N:11]=[C:12]([CH3:24])[N:13]=[C:14]([CH2:15][N:16]4[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]4[CH2:22][O:23][CH3:26])[C:9]=3[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 118023447HCID 118023447, compound

Product 1

HCID 118022971HCID 118022971, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of {(3S)-4-[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]morpholin-3-yl}methanol (132 mg) and DMF was added NaH (60% oil, 15 mg) under ice-cooling, followed by stirring at the same temperature for 5 minutes, and then CH3I (17 μL) was added thereto, followed by stirring at the same temperature for 30 minutes. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was washed with brine, then dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by basic silica gel column (hexane/EtOAc) to obtain 6-cyclohexyl-4-{[(3S)-3-(methoxymethyl)morpholin-4-yl]methyl}-2-methylthieno[2,3-d]pyrimidine (102 mg).

Workup

  1. temperaturecooling
  2. stirringby stirring at the same temperature for 30 minutes
  3. extractionfollowed by extraction with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-240c2bdee1b0400f8f161163fd24894f
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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