Ethanol → 5-Fluoro-2-(4-((2-phenyl-1H-imidazol-5-yl)methyl)-1-piperazinyl)pyrimidine

HRID 1075655Notes

Reaction equation

[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(O[CH2:18][C:19]1[NH:23][C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:21][CH:20]=1)(=O)C.C1(C)C=CC=CC=1.C(O)C>CN(C1C=CN=CC=1)C.O.C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH2:18][C:19]3[NH:23][C:22]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[N:21][CH:20]=3)[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 52.5 °C

Procedure

Mix 5-fluoro-2-piperazinyl-pyrimidine (900 g), 5-acetoxymethyl-2-phenyl-1H-imidazole (1.17 Kg, 1.1 equivalents), DMAP (N,N-dimethylaminopyridine, 30 g), toluene (7.2 L), ethanol (1.8 L) and triethylamine (1.095 L) at 20-25° C., and heat the mixture with stirring at 50-55° C. until the reaction is complete (typically about 20-25 hours). Then add water (3.75 L) and cool the resulting suspension to 0-50° C. Filter off the product, wash it with water (6×1.4 L) and cold toluene (3×700 ml), and dry it under vacuum at 50-55° C. to constant weight.

Workup

temperatureheat the mixture
customtypically about 20-25 hours
filtrationFilter off the product
washwash it with water (6×1.4 L) and cold toluene (3×700 ml)
customdry it under vacuum at 50-55° C. to constant weight

Sources & evidence

ORD record: ord-4b1a142c08cc47d195f3dbf3af683da3
Source dataset: uspto-grants-1999_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05905152

Reaction notes

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