(4-Fluoro-3-methylphenyl)methanamine → HCID 54697532, compound

HRID 458703Notes

Reaction equation

HRID 458703 reaction equation
[CH3:1][N:2]1[C:7]2=[N:8][C:9]([C:14]([O:16]CC)=O)=[C:10]([OH:13])[C:11](=[O:12])[N:6]2[CH2:5][C:4](=[O:19])[N:3]1[CH3:20].[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][C:23]=1[CH3:30]>>[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:27][C:14]([C:9]2[N:8]=[C:7]3[N:6]([C:11](=[O:12])[C:10]=2[OH:13])[CH2:5][C:4](=[O:19])[N:3]([CH3:20])[N:2]3[CH3:1])=[O:16])=[CH:24][C:23]=1[CH3:30]

Participants

3

Reactant 2

HCID 2774599(4-Fluoro-3-methylphenyl)methanamineHCID 54725630HCID 54725630, compound

Product 1

HCID 54697532HCID 54697532, compoundYield 79.8%

Procedure

Reaction of intermediate 22, ethyl 1,2-dimethyl-7-hydroxy-3,6-dioxo-2,3,4,6-tetrahydro-1H-pyrimido[2,1-c][1,2,4]triazine-8-carboxylate, (0.050 g, 0.177 mmol) with 4-fluoro-3-methylbenzylamine (0.10 g, 0.72 mmol) as described in the preparation of example 1 gave 0.053 g (79% yield) of the title amide as white crystals. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.31 (3H, s, CH3), 3.27 (3H, s, NCH3), 3.30 (3H, s, NCH3), 4.56 (2H, d, J=5.9 Hz, NCH2), 4.67 (2H, s, CH2), 7.02 (1H, m, aromatic), 7.14 (1H, m, aromatic), 7.17 (1H, m, aromatic), 7.71 (1H, broad t, NH), 12.02 (1H, s, OH). MS (ESI+) m/z 376 [M+H+].

Workup

  1. customas described in the preparation of example 1

Sources & evidence

ORD record
ord-3230886a8c9e4fde8d7659b8000ca591
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Reaction notes

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