(4-Fluoro-3-methylphenyl)methanamine → n-(4-Fluoro-3-methylbenzyl)-6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamide

HRID 458697Notes

Reaction equation

HRID 458697 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.[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][C:21]=1[CH3:28]>>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:25][C:14]([C:3]2[N:4]=[C:5]3[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:6]3[C:7](=[O:8])[C:2]=2[OH:1])=[O:16])=[CH:22][C:21]=1[CH3:28]

Participants

3

Reactant 2

HCID 2774599(4-Fluoro-3-methylphenyl)methanamineHCID 54725632Ethyl 6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate

Product 1

HCID 54687477n-(4-Fluoro-3-methylbenzyl)-6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamideYield 61.6%

Procedure

Reaction of intermediate 13, ethyl 6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate (0.050 g, 0.197 mmol) with 4-fluoro-3-methylbenzylamine (0.10 g, 0.72 mmol) as described in the preparation of example 1 gave 0.042 g (61% yield) of the title amide as a white solid. 1HNMR 400 MHz (DMSO-d6) δ (ppm): 2.21 (3H, d, J=1.5 Hz, CH3), 3.15 (3H, s, NCH3), 4.45 (2H, d, J=6.6 Hz, NCH2), 4.48 (2H, s, CH2), 7.05–7.25 (3H, m, aromatics), 9.45 (1H, broad t, NH), 12.29 (1H, s, OH). MS (ESI+) m/z 347 [M+H+].

Workup

  1. customas described in the preparation of example 1

Sources & evidence

ORD record
ord-52bc5e0f78a145bd9ba382891809e19c
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Reaction notes

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