Sodium hydride → 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzaldehyde

HRID 500646Notes

Reaction equation

HRID 500646 reaction equation
[H-].[Na+].[I:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[N:10][C:11]=2[NH2:13])[NH:6][N:5]=1.F[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1>CN(C=O)C>[NH2:13][C:11]1[N:10]=[CH:9][N:8]=[C:7]2[N:6]([C:15]3[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=3)[N:5]=[C:4]([I:3])[C:12]=12

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 680234-FluorobenzaldehydeHCID 178508725HCID 178508725, compound

Product 1

HCID 223468554-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)benzaldehydeYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a slurry of NaH (1.68 g, 42.1 mmol, 60% in oil) in 300 mL of DMF at RT, was added 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (10 g, 38.3 mmol) via a solid addition funnel over 45 min. After addition of the amine was complete, 4-fluorobenzaldehyde (5.0 g, 40.2 mmol) was added dropwise to the reaction mixture. The reaction was heated to 100° C. for 24 hr, an additional NaH (0.25 equivalents) was added and the mixture stirred at 100° C. for another 24 hr. The reaction was cooled to RT for 2 hr, a precipitate formed upon cooling. The reaction mixture was filtered, washed sequentially with water, then Et2O to afford a tan solid, 6.5 g, 47% yield.

Workup

  1. additionvia a solid addition funnel over 45 min
  2. temperatureThe reaction was cooled to RT for 2 hr
  3. customa precipitate formed
  4. temperatureupon cooling
  5. filtrationThe reaction mixture was filtered
  6. washwashed sequentially with water
  7. customEt2O to afford a tan solid, 6.5 g, 47% yield

Sources & evidence

ORD record
ord-3192bb761ccb435fa451a32783a370c2
Source dataset
uspto-grants-2010_08
Patent number
US07772231B2

Reaction notes

Loading…