4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine → 4-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

HRID 1398658Notes

Reaction equation

HRID 1398658 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:25])([Cl:24])[CH2:19]C(=N)OC>C(O)(=O)C.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:19]([C:18]([Cl:25])([Cl:24])[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

5

Reactant 2

HCID 681818104-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamineHCID 86669608Methyl 3,3,3-trichloropropanimidate

Product 1

HCID 681818334-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amineYield 81.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine (16.5 g, 58.90 mmol) in acetic acid (55 mL) was added methyl 2,2,2-trichloroethanecarboximidate (11 g, 62.35 mmol) dropwise with stirring. The reaction mixture was stirred at room temperature for 3 hr and then at 45° C. overnight. The resulting solution was diluted with 100 mL of water and the precipitate was collected by filtration. The solid was dried in a vacuum oven to give 19.5 g (81%) of 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine as a light brown solid: 1H NMR (300 MHz, DMSO) delta 8.58 (d, J=4.8 Hz, 1H), 7.68 (t, J=4.5 Hz, 1H), 7.61-7.58 (m, 2H), 7.21 (s, 2H), 7.01 (d, J=5.1 Hz, 3H); LC-MS: m/z=+408 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hr
  2. customat 45° C.
  3. customovernight
  4. filtrationthe precipitate was collected by filtration
  5. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-22821a84c58141618fb575f5ee40288c
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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