Sodium ethoxide → tert-Butyl 4-benzyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1930592Notes

Reaction equation

HRID 1930592 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[NH:15])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.O=[C:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]1[C:31](=O)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[O-]CC.[Na+]>C(O)C>[CH2:32]([C:31]1[C:19]2[CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23][C:18]=2[N:15]=[C:14]([NH:13][C:10]2[CH:9]=[CH:8][C:7]([N:3]3[CH:4]=[CH:5][N:6]=[C:2]3[CH3:1])=[CH:12][CH:11]=2)[N:16]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 59333761Tert-butyl 4-oxo-3-(2-phenylacetyl)piperidine-1-carboxylateHCID 178432900HCID 178432900, compound

Product 1

HCID 59333817tert-Butyl 4-benzyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylateYield 54.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-(2-Methyl-1H-imidazol-1-yl)phenyl)guanidine (224 mg, 1.04 mmol), tert-butyl 4-oxo-3-(2-phenylacetyl)piperidine-1-carboxylate (330 mg, 1.04 mmol) and sodium ethoxide (70.8 mg, 1.04 mmol) in ethanol (5 mL) were heated to 110° C. in a microwave reactor for 1 h 20 min. The reaction was allowed to reach room temperature and the solvent was evaporated under reduced pressure. The crude was dissolved in ethyl acetate and washed with water. The organic phase was dried under MgSO4 and the solvent evaporated under reduced pressure yielding tert-butyl 4-benzyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (280 mg, 54.2%) which was used in the subsequent step as such.

Workup

  1. customto reach room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe crude was dissolved in ethyl acetate
  4. washwashed with water
  5. customThe organic phase was dried under MgSO4
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-e33cb999738c479a90f0731ad8c050ba
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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