Formaldehyde → 3-Methyl-2-(1-methylpiperidin-4-yl)-6-(pyridin-4-yl)pyrimidin-4(3H)-one

HRID 1826522Notes

Reaction equation

HRID 1826522 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:4]=[C:3]1[CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[C:21](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>CO.C(O)(=O)C>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:4]=[C:3]1[CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 221396073-Methyl-2-(piperidin-4-yl)-6-(pyridin-4-yl)pyrimidin-4(3H)-one

Product 1

HCID 221395743-Methyl-2-(1-methylpiperidin-4-yl)-6-(pyridin-4-yl)pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

To a stirring solution of 3-methyl-2-piperidin-4-yl-6-pyridin-4-yl-3H-pyrimidin-4-one (0.74 mmol) in methanol/acetic acid was added sodium triacetoxyborohydride (1.1 mmol) and 0.5 mL of 37% aqueous formaldehyde. The reaction was stirred at room temperature for 30 min. The solvent was removed under vacuum and the residue partitioned between dichloromethane and 1N NaOH. The product was purified on silica. M+1=284.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue partitioned between dichloromethane and 1N NaOH
  3. customThe product was purified on silica

Sources & evidence

ORD record
ord-6e88be6632104a4787397f9cec6ea41b
Source dataset
uspto-grants-2006_05
Patent number
US07049318B2

Reaction notes

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