Methylamine → N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N,N2-dimethylglycinamide

HRID 1668402Notes

Reaction equation

HRID 1668402 reaction equation
Cl[CH2:2][C:3]([N:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]2[C:21](=[O:22])[C:20]3[S:23][C:24]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)=[CH:25][C:19]=3[N:18]=[CH:17]2)=[CH:10][CH:9]=1)[CH3:6])=[O:4].[CH3:33][NH2:34]>CO.CN(C)C=O.C(OCC)(=O)C>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([C:24]2[S:23][C:20]3[C:21](=[O:22])[N:16]([CH2:15][CH2:14][C:11]4[CH:12]=[CH:13][C:8]([CH2:7][N:5]([CH3:6])[C:3](=[O:4])[CH2:2][NH:34][CH3:33])=[CH:9][CH:10]=4)[CH:17]=[N:18][C:19]=3[CH:25]=2)=[CH:27][CH:28]=1

Participants

6

Reactant 2

HCID 6329MethylamineHCID 592398302-chloro-N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N-methylacetamide

Product 1

HCID 59239845N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N,N2-dimethylglycinamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the compound (0.12 g) obtained in Example 27, 40% methylamine in methanol solution (0.28 ml) and N,N-dimethylformamide (2 ml) was stirred at room temperature for 1 hr, diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane (1:1, volume ratio) to give the title compound (53 mg) as a colorless powder.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from ethyl acetate-hexane (1:1, volume ratio)

Sources & evidence

ORD record
ord-bc8166d171034202b405a64e4d4dbd83
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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