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

HRID 1930639Notes

Reaction equation

HRID 1930639 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)[CH:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:33].[O-]CC.[Na+]>C(O)C>[CH3:1][C:2]1[N:3]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]3[N:16]=[C:31]([CH:32]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH3:33])[C:19]4[CH2:20][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:22][CH2:23][C:18]=4[N:15]=3)=[CH:11][CH:12]=2)[CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 59333793Tert-butyl 4-oxo-3-(2-phenylpropanoyl)piperidine-1-carboxylateHCID 178432900HCID 178432900, compound

Product 1

HCID 59333787tert-Butyl 2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-4-(1-phenylethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylateYield 36.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-(2-Methyl-1H-imidazol-1-yl)phenyl)guanidine (700 mg, 3.25 mmol, example 9e), tert-butyl 4-oxo-3-(2-phenylpropanoyl)piperidine-1-carboxylate (1293 mg, 3.90 mmol) and sodium ethoxide (221 mg, 3.25 mmol) in ethanol (6 mL) were heated to 110° C. in a microwave reactor for 4 h. The solvent was evaporated and the crude was dissolved in ethyl acetate and washed with water. The organic phase was dried under MgSO4 and the solvent was evaporated under reduced pressure. Purification by flash chromatography using dichloromethane and methanol (0-10%) as eluent gave tert-butyl 2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-4-(1-phenylethyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (612 mg, 36.9%). MS (ES+) m/z 511 (M+H)+

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude was dissolved in ethyl acetate
  3. washwashed with water
  4. customThe organic phase was dried under MgSO4
  5. customthe solvent was evaporated under reduced pressure
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-362d50f8d5be4483864e900909fdaf7d
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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