Cyclohexanemethanol → HCID 17941787、化合物

HRID 1838965ノート

反応式

HRID 1838965 の反応式
[Na].[CH:2]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[NH2:10][C:11]1[N:16]=[C:15](Cl)[CH:14]=[C:13]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:12]=1>>[NH2:10][C:11]1[N:16]=[C:15]([O:9][CH2:8][CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH:14]=[C:13]([NH:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:12]=1

参加物

4

反応物 3

HCID 7507CyclohexanemethanolHCID 14842704-N-benzyl-6-chloropyrimidine-2,4-diamineHCID 5360545Sodium

生成物 1

HCID 17941787HCID 17941787、化合物収率 49%

反応条件

温度
180 °C

実験手順

To a stirred solution of sodium (0.025 g, 1.09 mmol) in cyclohexylmethanol (5 ml, 43 mmol) under nitrogen at 100° C., was added 2-amino-6-benzylamino-4-chloropyrimidine (0.2 g, 0.86 mmol), and the mixture was stirred at 180° C. for 2 h. After removal of solvents, the residue was redissolved in methanol, filtered and the filtrate was evaporated to dryness. The crude product was purified by chromatography on silica, employing petrol: ethyl acetate (8:2) as eluent, to give the title product as a yellow solid (0.13 g, 49%); δH (200 MHz, d6-DMSO) 0.96-1.15 (5H, m, C6H11), 1.23-1.34 (6H, m, C6H11), 4.03 (2H, br s, OCH2), 4.51 (2H, d, C6H5CH2, J=5.31 Hz), 5.12 (1H, s, C(5)H), 6.56 (2H, br s, NH2), 7.20 (1H, br s, NH), 7.28-7.39 (5H, m, C6H5); m/z (+EI) 312 (M+, 100%), 229 (M+-C6H11, 45), 216 (MH+-C6H11CH2, 53), 91 (72).

後処理

  1. customAfter removal of solvents
  2. dissolutionthe residue was redissolved in methanol
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness
  5. customThe crude product was purified by chromatography on silica

出典と根拠

ORDレコード
ord-e69919f19d354e06860fc4951b80b2b0
出典データセット
uspto-grants-2004_01
特許番号
US06677345B1

反応ノート

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