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

HRID 2047668노트

반응식

HRID 2047668 반응식
[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

참가 물질

7

반응물 4

HCID 6212ChloroformHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 178506017HCID 178506017, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

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].

후처리

  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)

출처 및 근거

ORD 기록
ord-ed6e66ef5e3649ca9385e9b5a021ae4c
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592581B2

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