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

HRID 2245220

반응식

HRID 2245220 반응식
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]

참가 물질

5

반응물 2

HCID 768044-(Trifluoromethyl)benzylamineHCID 2274594-Amino-2-chloro-6-methyl-5-nitropyrimidine

생성물 1

HCID 592160226-Methyl-5-nitro-N*2*-(4-trifluoromethylbenzyl)-pyrimidine-2,4-diamine수율 94.1%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-c294ef0dc8244a38931202f8a08200ca
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07683058B2

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