Ammonium Hydroxide → 4-N-(5-bromo-2-nitrophenyl)pyrimidine-2,4-diamine

HRID 1398502Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11](Cl)[N:10]=2)[CH:7]=1.[OH-].[NH4+:20]>CC(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:20])[N:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of N-(5-bromo-2-nitrophenyl)-2-chloropyrimidin-4-amine (6 g, 18.21 mmol) in 2-propanol (70 mL), in a pressure vessel, was carefully added ammonium hydroxide solution (150 mL) at RT. The reaction vessel was sealed and stirred at 90° C. (at 4.5 bar pressure) for 20 hr. The reaction mixture was cooled to 0° C. The resulting precipitate was collected by vacuum filtration, washed with water and dried in the vacuum oven to afford the title compound as an orange solid: 1H NMR (250 MHz, DMSO) δ 6.17 (1H, d, J=5.63 Hz), 6.34 (2H, br. s.), 7.39 (1H, dd, J=8.83, 1.98 Hz), 7.89-7.99 (2H, m), 8.34 (1H, d, J=2.13 Hz), 9.62 (1H, s); LC-MS: m/z+309.9, 311.7 (M+H)+.

Workup

customat RT
customThe reaction vessel was sealed
temperatureThe reaction mixture was cooled to 0° C
filtrationThe resulting precipitate was collected by vacuum filtration
washwashed with water
customdried in the vacuum oven

Sources & evidence

ORD record: ord-c852f738cd874053b847da34a32d27f9
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901313B2

Reaction notes

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