Formaldehyde → 3-iodo-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 432466Notes

Reaction equation

HRID 432466 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[N:3]=1.C=O.[C:20](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+].[OH-].[Na+]>ClC(Cl)C>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH:12]2[CH2:17][CH2:16][N:15]([CH3:20])[CH2:14][CH2:13]2)[N:3]=1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 223466933-Iodo-1-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 223471833-iodo-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 53%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

3-Iodo-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.5 g, 1.45 mmol), formaldehyde (30% in water, 0.16 mL, 1.60 mmol) and sodium triacetoxyborohydride (0.43 g, 2.03 mmol) was mixed in dichloroethane (5 mL). After 4 hours, saturated sodium bicarbonate was added followed by sodium hydroxide (1.0N) to bring the pH to 10. The aqueous layer was extracted with dichloromethane. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated to give 3-iodo-1-(1-methyl-4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.275 g, 53%). 1H NMR (DMSO-d6) δ 1.85 (m, 2H), 2.09 (m, 4H), 2.22 (s, 3H), 2.88 (m, 2H), 4.75 (m, 1H), 8.19 (s, 1H), 8.32 (s, 1H).

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d556056e48ee4f8ab0e448b668e56b74
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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