Acetic Anhydride → 1-(4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone

HRID 1930711Notes

Reaction equation

HRID 1930711 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([C:15]1[C:16]2[CH2:39][NH:38][CH2:37][CH2:36][C:17]=2[N:18]=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]3)=[C:24]([O:34][CH3:35])[CH:23]=2)[N:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[CH2:8]([C:15]1[C:16]2[CH2:39][N:38]([C:1](=[O:3])[CH3:2])[CH2:37][CH2:36][C:17]=2[N:18]=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]3)=[C:24]([O:34][CH3:35])[CH:23]=2)[N:20]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 593336984-Benzyl-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Product 1

HCID 593337471-(4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanoneYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic anhydride (0.039 mL, 0.41 mmol) was added to a solution of 4-benzyl-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (175 mg, 0.41 mmol, example 109) in THF (3 mL) and stirred for one hour. The solvent was evaporated under reduced pressure and the crude product purified on prepHPLC yielding 1-(4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone (64.0 mg, 33.3%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude product purified

Sources & evidence

ORD record
ord-a6dbd0a427d644208dc39cac8b71494b
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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