Tert-butyl 4-oxo-3-(2-p-tolylacetyl)piperidine-1-carboxylate → tert-Butyl 2-(4-(2-methyl-1H-imidazol-1-yl)phenyl amino)-4-(4-methylbenzyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1930606Notes

Reaction equation

HRID 1930606 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[C:15](=O)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1.[CH3:25][C:26]1[N:27]([C:31]2[CH:36]=[CH:35][C:34]([NH:37][C:38]([NH2:40])=[NH:39])=[CH:33][CH:32]=2)[CH:28]=[CH:29][N:30]=1>>[CH3:25][C:26]1[N:27]([C:31]2[CH:32]=[CH:33][C:34]([NH:37][C:38]3[N:39]=[C:15]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)[C:3]4[CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7][C:2]=4[N:40]=3)=[CH:35][CH:36]=2)[CH:28]=[CH:29][N:30]=1

Participants

3

Reactant 2

HCID 59333812Tert-butyl 4-oxo-3-(2-p-tolylacetyl)piperidine-1-carboxylateHCID 178432900HCID 178432900, compound

Product 1

HCID 59333746tert-Butyl 2-(4-(2-methyl-1H-imidazol-1-yl)phenyl amino)-4-(4-methylbenzyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylateYield 44%

Procedure

tert-Butyl 2-(4-(2-methyl-1H-imidazol-1-yl)phenyl amino)-4-(4-methylbenzyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (236 mg, 44%) was synthesised from tert-butyl 4-oxo-3-(2-p-tolylacetyl)piperidine-1-carboxylate and 1-(4-(2-methyl-1H-imidazol-1-yl)phenyl)guanidine (Example 41c) according to the general procedure for synthesis of pyrimidines. MS (ES+) m/z 511.1 (M+H)+

Sources & evidence

ORD record
ord-896451ef61a64e2cba49bb2f62523a68
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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