2-Methyl-2-butene → HCID 68964709, compound

HRID 1396552Notes

Reaction equation

HRID 1396552 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:21])[N:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=3[O:19][CH3:20])[CH:14]=[O:15])[C:5]2=[CH:4][N:3]=1.CC(=CC)C.Cl([O-])=[O:28].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O>[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:21])[N:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=3[O:19][CH3:20])[C:14]([OH:28])=[O:15])[C:5]2=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86630405HCID 86630405, compound

Product 1

HCID 68964709HCID 68964709, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

3-(6-Amino-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-4-methoxy-benzaldehyde (Example 75) (0.5 g, 1.77 mmol) is suspended in t-butanol (12 ml) and 2-methyl-2-butene (0.562 ml, 5.31 mmol). To this is added a solution of sodium chlorite (0.367 g, 4.06 mmol) and sodium dihydrogen phosphate (0.848 g, 7.06 mmol) in water (5 ml). The reaction mixture is stirred at room temperature for 48 hours and the resulting precipitate is collected by filtration, dissolved in saturated aqueous NaHCO3 (100 ml) and washed with EtOAc (2×50 ml). The aqueous portion is acidified to pH1 with 2M HCl resulting in an off-white solid which is collected by filtration and dried under vacuum for 72 hours to afford the title compound.

Workup

  1. filtrationthe resulting precipitate is collected by filtration
  2. dissolutiondissolved in saturated aqueous NaHCO3 (100 ml)
  3. washwashed with EtOAc (2×50 ml)
  4. filtrationis collected by filtration
  5. customdried under vacuum for 72 hours

Sources & evidence

ORD record
ord-8351219475ee417ea3dd0ddac159fdf0
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

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