2-Nitroaniline → N-Methyl-N'-(2-nitro-phenyl)-pyrimidine-4,6-diamine

HRID 58127

反応式

HRID 58127 の反応式
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH3:9])[CH:3]=1.[N+:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19])([O-:12])=[O:11].CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=C(OC)C=CC=2OC)=C(C(C)C)C=1)C.CC([O-])(C)C.[Na+]>COCCOC.CCOC(C)=O>[CH3:9][NH:8][C:4]1[CH:3]=[C:2]([NH:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N+:10]([O-:12])=[O:11])[N:7]=[CH:6][N:5]=1

参加物

7

反応物 4

HCID 69462-NitroanilineHCID 3094796-chloro-N-methylpyrimidin-4-amineHCID 23676156Sodium t-butoxideHCID 25112535Brettphos

生成物 1

HCID 118025224N-Methyl-N'-(2-nitro-phenyl)-pyrimidine-4,6-diamine収率 35%

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

A mixture of (6-chloro-pyrimidin-4-yl)-methyl-amine (1 g, 7 mmol), 2-nitro-phenylamine (965 mg, 7 mmol), Brettphos (279 g, 0.35 mmol) and tBuONa (2 g, 21 mmol) in DME (50 mL) was heated to 90° C. for 1 hour under nitrogen atmosphere. The reaction was concentrated, and the residue was purified by flash chromatography on silica eluting with DCM:EtOAc=10:1-4:1 to obtain the title compound (600 mg, yield: 35%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 2.94 (d, 3H), 4.99 (bs, 1H), 5.82 (s, 1H), 7.04 (t, 1H), 7.60 (t, 1H), 8.21 (d, 1H), 8.33 (s, 1H), 8.75 (d, 1H), 9.91 (s, 1H); MS (ESI): 246 [M+H]+.

後処理

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by flash chromatography on silica eluting with DCM

出典と根拠

ORDレコード
ord-dbc33cc138c8488da1bb47f71f9ebd37
出典データセット
uspto-grants-2016_09
特許番号
US09434697B2

関連ノート

読み込み中…