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

HRID 72705

Reaction equation

HRID 72705 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-556b893a729546d8a1b1ce2dd4e70ef2
Source dataset
uspto-grants-2014_09
Patent number
US08829010B2

Linked notes

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