4-(Trifluoromethyl)benzylamine → 6-Methyl-5-nitro-N2-(4-trifluoromethylbenzyl)-pyrimidine-2,4-diamine

HRID 2245220Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:12])[N:3]=1.[F:13][C:14]([F:24])([F:23])[C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1>C(#N)C.C(N(CC)CC)C>[CH3:12][C:4]1[N:3]=[C:2]([NH:20][CH2:19][C:18]2[CH:17]=[CH:16][C:15]([C:14]([F:13])([F:23])[F:24])=[CH:22][CH:21]=2)[N:7]=[C:6]([NH2:8])[C:5]=1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-chloro-6-methyl-5-nitropyrimidin-4-ylamine (300 mg, 1.591 mmol), 4-trifluoromethylbenzylamine (369 mg, 2.107 mmol) in acetonitrile (3 ml) and triethylamine (0.5 ml) were flashed with argon, sealed in the Emrys process vial and heated at 120° C. for 2 min under microwave irradiation. The obtained suspension was quenched with 10% aqueous sodium carbonate (2 ml) and organic volatiles were evaporated under reduced pressure. Methanol (5 ml) and water (100 ml) were added to the residue. The product was separated by filtration, washed with water and dried in vacuo to give 490 mg of yellow solid. Yield 94%. LC-MS (m/z) 328.1 (MH+); tR=2.58. 1H NMR (500 MHz, DMSO-d6): ca. 3:1 mixture of two rotamers, 2.54 (s, 3H), 4.57 (d, 1.5H), 4.63 (d, 0.5H), 7.52 (t, 2H), 7.68 (d, 2H), 7.81 (s, 0.5H, NH2), 8.0 (s, 1.5H, NH2), 8.17 (t, 0.25H, NH), 8.48 (t, 0.75H, NH).

Workup

customsealed in the Emrys process vial
customThe obtained suspension was quenched with 10% aqueous sodium carbonate (2 ml) and organic volatiles
customwere evaporated under reduced pressure
additionMethanol (5 ml) and water (100 ml) were added to the residue
customThe product was separated by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-c294ef0dc8244a38931202f8a08200ca
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683058B2

Reaction notes

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