Morpholine → 1-methyl-2-[1-(2-morpholin-4-ylmethyl-phenyl)piperidin-4-yloxy]-1H-[4,4']bipyrimidinyl-6-one

HRID 1468780Notes

Reaction equation

HRID 1468780 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:29]=[CH:28][CH:27]=[CH:26][C:23]=2[CH:24]=O)[CH2:18][CH2:17]1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C(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[CH2:17][CH2:18][N:19]([C:22]2[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=2[CH2:24][N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 866691462-[4-(1-Methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yloxy)piperidin-1-yl]benzaldehyde

Product 1

HCID 681601281-methyl-2-[1-(2-morpholin-4-ylmethyl-phenyl)piperidin-4-yloxy]-1H-[4,4']bipyrimidinyl-6-oneYield 70%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 2-[4-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yloxy)piperidin-1-yl]benzaldehyde (80 mg, 0.20 mmol), morpholine (27 mg 0.31 mmol) and acetic acid (one drop) in 1,2-dichloroethane (1.0 ml) was added sodium triacetoxyborohydride (110 mg, 0.52 mmol). The mixture was stirred at room temperature for 2 hours. The mixture was partitioned between water and chloroform. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, 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-(2-morpholin-4-ylmethyl-phenyl)piperidin-4-yloxy]-1H-[4,4′]bipyrimidinyl-6-one as a colorless solid (63 mg, 0.14 mmol, 67%).

Workup

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

Sources & evidence

ORD record
ord-4660a910661047fca6cd6a0958afab16
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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