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

HRID 1930708Notes

Reaction equation

HRID 1930708 reaction equation
Br[CH2:2][C:3]#[N:4].[CH2:5]([C:12]1[C:13]2[CH2:36][NH:35][CH2:34][CH2:33][C:14]=2[N:15]=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]3)=[C:21]([O:31][CH3:32])[CH:20]=2)[N:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1>[CH2:5]([C:12]1[C:13]2[CH2:36][N:35]([CH2:2][C:3]#[N:4])[CH2:34][CH2:33][C:14]=2[N:15]=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]3)=[C:21]([O:31][CH3:32])[CH:20]=2)[N:17]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 11534BromoacetonitrileHCID 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 593337672-(4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)acetonitrileYield 37.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Bromoacetonitrile (0.031 mL, 0.45 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 106) and TEA (0.063 mL, 0.45 mmol) in THF (3 mL). The solution was stirred at RT for 2 hours. Solvent was evaporated and the crude product was purified on a prepHPLC yielding 2-(4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)acetonitrile (72.0 mg, 37.7%). MS (ES+) m/z 466.3 (M+H)+

Workup

  1. customSolvent was evaporated
  2. customthe crude product was purified on

Sources & evidence

ORD record
ord-e6c2fe5818c64279ad9d1e9f44056828
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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