Water → 4-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

HRID 1398648Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=1.[Cl:17][C:18]([Cl:24])([Cl:23])[C:19](=N)OC.O>C(O)(=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:19]([C:18]([Cl:24])([Cl:23])[Cl:17])[N:9]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=3)[C:3]=2[CH:4]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine (3.0 g, 10.71 mmol) in acetic acid (10 mL) was added methyl 2,2,2-trichloroethanimidoate (1.4 mL, 11.25 mmol). The reaction was stirred at 45° C. for 7 hr. Water (15 mL) was then added. The precipitate was collected by filtration and dried under vacuum to give the title product (3.94 g as the acetic acid salt); 1H NMR (500 MHz, DMSO) delta 1.90 (3H, s), 7.01 (1H, d, J=5.0 Hz), 7.21 (2H, s), 7.75-7.46 (2H, m), 8.09-7.75 (1H, m), 8.58 (1H, d, J=5.0 Hz); LC-MS: m/z=+406/408/410/412 (M+H)+.

Workup

filtrationThe precipitate was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-218e4a7a11994dfda8b805c117e9310a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901313B2

Reaction notes

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