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

HRID 2245220

反応式

HRID 2245220 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c294ef0dc8244a38931202f8a08200ca
出典データセット
uspto-grants-2010_03
特許番号
US07683058B2

関連ノート

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