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

HRID 1668405Notes

Reaction equation

HRID 1668405 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:34]=[CH:33][C:25]([CH2:26][N:27]([CH3:32])[CH2:28][C:29](O)=[O:30])=[CH:24][CH:23]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1.CN.[CH2:37]([N:39](CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>O1CCCC1.C(OCC)(=O)C.C(Cl)Cl>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][C:25]([CH2:26][N:27]([CH3:32])[CH2:28][C:29]([NH:39][CH3:37])=[O:30])=[CH:33][CH:34]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 67360373N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N-methylglycine dihydrochloride

Product 1

HCID 59239837N2-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N,N2-dimethylglycinamideYield 22.5%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the compound (70 mg) obtained in Example 30, 2N methylamine in tetrahydrofuran solution (0.65 ml), triethylamine (59 mg), bis(2-oxo-3-oxazolidinyl)phosphinoyl chloride (39 mg) and methylene chloride (5 ml) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated is under reduced pressure. The residue was purified by column chromatography [developing solvent:ethyl acetate-methanol (10:1, volume ratio)] and recrystallized from ethyl acetate-hexane (1:1, volume ratio) to give the title compound (14 mg) as a colorless powder.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography [developing solvent:ethyl acetate-methanol (10:1, volume ratio)]
  5. customrecrystallized from ethyl acetate-hexane (1:1, volume ratio)

Sources & evidence

ORD record
ord-3166cb4fe9ba44f7a45eaa8170f60c8f
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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