Benzenemethanamine, 3-chloro-4-methyl- → HCID 54680190, compound

HRID 1822717Notes

Reaction equation

HRID 1822717 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=2[O:23][CH3:24])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=[O:5])C.[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[CH3:34])[CH2:29][NH2:30]>>[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[CH3:34])[CH2:29][NH:30][C:4]([C:6]1[N:7]=[C:8]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=2[O:23][CH3:24])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=[O:5]

Participants

3

Reactant 2

HCID 106225Benzenemethanamine, 3-chloro-4-methyl-HCID 54691439HCID 54691439, compound

Product 1

HCID 54680190HCID 54680190, compound

Procedure

Prepared according to the procedure described for example 2 from 2-(2,6-dimethoxy-phenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (50 mg, 0.15 mmol) and 3-chloro-4-methylbenzylamine (107 mg, 0.75 mmol). The title product was obtained as a pink solid (51.1 mg, 77% yield). 1HNMR (500 MHz, CDCl3) δ: 12.09 (1H, s), 7.92 (1H, t, J=5.50 Hz), 7.39 (1H, t, J=8.24 Hz), 7.28 (1H, d, J=1.22 Hz), 7.17 (1H, d, J=7.63 Hz), 7.10 (1H, dd, J=7.63, 1.53 Hz), 6.62 (2H, d, J=8.24 Hz), 4.49 (2H, d, J=6.40 Hz), 3.76 (6H, s), 3.28 (3H, s), 2.33 (3H, s). HRMS (ESI) calcd for C22H23ClN3O5 (M+H): 444.1326; found: 444.1327.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2f53b41276374f9695a92ac8056a97eb
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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