Chloroform → (2-Fluoro-9-isopropyl-9H-purin-6-yl)pyridine-4-ylmethylamine

HRID 2047668ノート

反応式

HRID 2047668 の反応式
[F:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:26]([CH3:28])[CH3:27].C(Cl)(Cl)Cl>CN(C=O)C.CO>[F:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:26]([CH3:28])[CH3:27])=[C:4]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:3]=1

参加物

7

反応物 4

HCID 6212ChloroformHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 178506017HCID 178506017、化合物

生成物 1

HCID 57433119(2-Fluoro-9-isopropyl-9H-purin-6-yl)pyridine-4-ylmethylamine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of (2-Fluoro-9H-purin-6-yl)-pyridin-4-ylmethyl-amine (0.6 g, 2.46 mmol) in DMF (10 mL) under an argon atmosphere, at RT, was added K2CO3 (powdered, anhydrous, 1.7 g, 5 eq, 12.3 mmol) followed by 2-bromopropane (2.3 ml, 10 eq, 24.6 mmol). The reaction mixture was stirred at RT for 24 h, when TLC (CHCl3:MeOH; 90:10) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue partitioned between water (200 ml) and EtOAc (50 ml). The aqueous phase was separated and extracted with more EtOAc (2×50 mL). The bulked organic phase was washed with brine (50 ml), dried (MgSO4) and evaporated in vacuo, and the residue was purified by gradient column chromatography on silica gel, eluted with chloroform:methanol (100:0→95:5), to provide the product as a white solid; Yield: 0.40 g (57%). mp 170-173° C. 1H-NMR (d6-DMSO, 250 MHz): δ 1.49 (6 H, d, J 7.5, —CH(CH3)2), 4.63 (3 H, m, —CH(CH3)2+—HNCH2-Pyr), 7.30, 8.47 (4 H, 2×m, Pyr-H), 8.28 (s, 1 H, —N═CH—N—), 8.97 (1 H, s, br, —HNCH2-Pyr). m/z: 287 ([M+H].

後処理

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between water (200 ml) and EtOAc (50 ml)
  3. customThe aqueous phase was separated
  4. extractionextracted with more EtOAc (2×50 mL)
  5. washThe bulked organic phase was washed with brine (50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customthe residue was purified by gradient column chromatography on silica gel
  9. washeluted with chloroform:methanol (100:0→95:5)

出典と根拠

ORDレコード
ord-ed6e66ef5e3649ca9385e9b5a021ae4c
出典データセット
uspto-grants-2013_11
特許番号
US08592581B2

反応ノート

読み込み中…