Benzenemethanamine, 3,4-dimethyl- → n-(3,4-Dimethylbenzyl)-6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamide

HRID 458699

Reaction equation

HRID 458699 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:9][C:10](=[O:13])[N:11]([CH3:12])[C:5]2=[N:4][C:3]=1[C:14]([O:16]CC)=O.[CH3:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[CH3:28])[CH2:23][NH2:24]>>[CH3:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[CH3:28])[CH2:23][NH:24][C:14]([C:3]1[N:4]=[C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:6]2[C:7](=[O:8])[C:2]=1[OH:1])=[O:16]

Participants

3

Reactant 2

HCID 66888Benzenemethanamine, 3,4-dimethyl-HCID 54725632Ethyl 6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate

Product 1

HCID 54704302n-(3,4-Dimethylbenzyl)-6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamideYield 58%

Procedure

Reaction of intermediate 13, ethyl 6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate (0.070 g, 0.28 mmol) with 3,4-dimethylbenzylamine (0.15 g, 1.12 mmol) as described in the preparation of example 1 gave 0.042 g (58% yield) of the title amide as a white solid. 1HNMR 400 MHz (DMSO-d6) δ (ppm): 2.18 (3H, s, CH3), 2.20 (3H, s, CH3), 3.14 (3H, s, NCH3), 4.42 (2H, d, J=6.3 Hz, NCH2), 4.47 (2H, s, CH2), 7.0–7.1 (3H, m, aromatics), 9.40 (1H, broad t, NH), 12.35 (1H, s, OH). MS (ESI+) m/z 343 [M+H+].

Workup

  1. customas described in the preparation of example 1

Sources & evidence

ORD record
ord-c6017042c8b2404ab0c98e074b43aa1d
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Linked notes

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