2,4-Diaminotoluene → N2,N4-bis(3-amino-4-methylphenyl)-5-fluoro-2,4-pyrimidinediamine

HRID 603657

反応式

HRID 603657 の反応式
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[CH3:18])[NH2:14]>CO.O>[NH2:10][C:11]1[CH:12]=[C:13]([NH:14][C:2]2[N:7]=[C:6]([NH:14][C:13]3[CH:15]=[CH:16][C:17]([CH3:18])=[C:11]([NH2:10])[CH:12]=3)[C:5]([F:9])=[CH:4][N:3]=2)[CH:15]=[CH:16][C:17]=1[CH3:18]

参加物

5

反応物 2

HCID 72612,4-DiaminotolueneHCID 2507052,4-Dichloro-5-fluoropyrimidine

生成物 1

HCID 22060880N2,N4-bis(3-amino-4-methylphenyl)-5-fluoro-2,4-pyrimidinediamine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

2,4-Dichloro-5-fluoropyrimidine (50 mg, 0.30 mmol) was dissolved in a mixture of MeOH (1 ml) and H2O (0.1 ml). 3-amino-4-methylaniline (146 mg, 1.2 mmol) was added and the mixture was refluxed for 20 hours (70° C. oil-bath temperature). The mixture was cooled to 22° C., concentrated to dryness under reduced pressure and subjected to column chromatography on silica gel (CHCl3-Acetone, 2:1) to give N2,N4-bis(3-amino-4-methylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 8.11 (d, 1H, J=5.1 Hz), 7.98 (bs, 1H) (7.68 (dd, 1H, J=2.4, 8.1 Hz), 7.40-7.55 (m, 4H), 2.43 (s, 3H), 2.42 (s, 3H); LCMS: purity: 95.0%; MS (m/e): 338.66 (M+, 70).

後処理

  1. temperatureThe mixture was cooled to 22° C.
  2. concentrationconcentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-da5c86f1e86044348ac87d8206db4584
出典データセット
uspto-grants-2011_03
特許番号
US07906644B2

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