Formaldehyde → 1-methyl-2-{1-[4-(4-methyl-piperazin-1-ylmethyl)phenyl]piperidin-4-yloxy}-1H-[4,4']bipyrimidinyl-6-one

HRID 1468778Notes

Reaction equation

HRID 1468778 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][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[CH:24][CH:23]=2)[CH2:18][CH2:17]1.C=O.[C:37](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCCl>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:23]=[CH:24][C:25]([CH2:28][N:29]3[CH2:34][CH2:33][N:32]([CH3:37])[CH2:31][CH2:30]3)=[CH:26][CH:27]=2)[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 509398121-methyl-2-[1-(4-piperazin-1-ylmethyl-phenyl)piperidin-4-yloxy]-1H-[4,4']bipyrimidinyl-6-one

Product 1

HCID 509398131-methyl-2-{1-[4-(4-methyl-piperazin-1-ylmethyl)phenyl]piperidin-4-yloxy}-1H-[4,4']bipyrimidinyl-6-oneYield 59%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 1-methyl-2-[1-(4-piperazin-1-ylmethyl-phenyl)piperidin-4-yloxy]-1H-[4,4′]bipyrimidinyl-6-one (80 mg, 0.17 mmol), formaldehyde solution (37% in water, 55 mg, 0.68 mmol) and acetic acid (one drop) in 1,2-dichloroethane (0.85 ml) was added sodium triacetoxyborohydride (130 mg, 0.61 mmol). The mixture was stirred at room temperature for 2 hours. The mixture was partitioned between water and chloroform. The organic layer was dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; chloroform/methanol=95/5) to afford 1-methyl-2-{1-[4-(4-methyl-piperazin-1-ylmethyl)phenyl]piperidin-4-yloxy}-1H-[4,4′]bipyrimidinyl-6-one as a colorless solid (49 mg, 0.10 mmol, 59%)

Workup

  1. customThe mixture was partitioned between water and chloroform
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (eluent; chloroform/methanol=95/5)

Sources & evidence

ORD record
ord-7517e539974b4bb782d13f08123d593b
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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