4-Fluorobenzylamine → HCID 54680621, compound

HRID 1822714Notes

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.[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1>>[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH:31][C:4]([C:6]2[N:7]=[C:8]([C:15]3[C:16]([O:23][CH3:24])=[CH:17][CH:18]=[CH:19][C:20]=3[O:21][CH3:22])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=2[OH:12])=[O:5])=[CH:28][CH:27]=1

Participants

Reactant 2

HCID 673264-Fluorobenzylamine

HCID 54691439HCID 54691439, compound

Product 1

HCID 54680621HCID 54680621, 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 4-fluorobenzylamine (125 mg, 1.0 mmol). The title product was obtained as a pink solid (48.7 mg, 79% yield). 1HNMR (500 MHz, CDCl3) δ: 12.10 (1H, s), 7.92 (1H, t, J=5.50 Hz), 7.39 (1H, t, J=8.54 Hz), 7.30 (1H, d, J=5.19 Hz), 7.28 (1H, d, J=5.19 Hz), 7.00 (2H, t, J=8.54 Hz), 6.62 (2H, d, J=8.24 Hz), 4.52 (2H, d, J=6.40 Hz), +3.75 (6H, s), 3.28 (3H, s). HRMS (ESI) calcd for C21H21FN3O5 (M+H): 414.1465; found: 414.1454.

Workup

customPrepared

Sources & evidence

ORD record: ord-5f1f7b8009f34503a69b44358f0b2bdc
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037908B2

Reaction notes

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