Sodium Bicarbonate → 4-(3-fluoroazetidin-1-yl)-3-iodo-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

HRID 72705

반응식

HRID 72705 반응식
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:12])[N:9]=[C:10]([I:11])[C:3]=12.[F:13][CH:14]1[CH2:17][NH:16][CH2:15]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[F:13][CH:14]1[CH2:17][N:16]([C:2]2[N:7]=[CH:6][N:5]=[C:4]3[N:8]([CH3:12])[N:9]=[C:10]([I:11])[C:3]=23)[CH2:15]1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 36035423-FluoroazetidineHCID 867125614-chloro-3-iodo-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

생성물 1

HCID 711144194-(3-fluoroazetidin-1-yl)-3-iodo-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-Chloro-3-iodo-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (C9) (2.00 g, 6.79 mmol), 3-fluoroazetidine (833 mg, 7.46 mmol), saturated aqueous sodium bicarbonate solution (30 mL), and tetrahydrofuran (40 mL) were combined and allowed to stir at room temperature for 18 hours. After removal of volatiles in vacuo, the residue was diluted with water. Filtration provided the product as a tan solid. Yield: 1.91 g, 5.73 mmol, 84%. LCMS m/z 334.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ 3.91 (s, 3H), 4.47-4.63 (m, 2H), 4.75-4.90 (m, 2H), 5.44-5.64 (m, 1H, JHF=58.0 Hz), 8.31 (s, 1H).

후처리

  1. customAfter removal of volatiles in vacuo
  2. additionthe residue was diluted with water
  3. filtrationFiltration

출처 및 근거

ORD 기록
ord-556b893a729546d8a1b1ce2dd4e70ef2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829010B2

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