Tetrahydrofuran → (S)-2-(3-(4-methoxybiphen-4-yl)piperazin-1-yl)-3-methyl-6-(4-pyridyl)pyrimidin-4-one

HRID 1784693Notes

Reaction equation

HRID 1784693 reaction equation
Cl.Cl.CO[C:5]1[CH:22]=[CH:21][C:8]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:20][NH:19][CH2:18][CH2:17][NH:16]3)=[CH:11][CH:10]=2)=[CH:7][CH:6]=1.C(N(CC)CC)C.Cl[C:31]1[N:36]([CH3:37])[C:35](=[O:38])[CH:34]=[C:33]([C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)[N:32]=1.[O:45]1CCC[CH2:46]1>>[CH3:46][O:45][C:12]1([C@H:15]2[NH:16][CH2:17][CH2:18][N:19]([C:31]3[N:36]([CH3:37])[C:35](=[O:38])[CH:34]=[C:33]([C:39]4[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=4)[N:32]=3)[CH2:20]2)[CH:11]=[CH:10][C:9]([C:8]2[CH:7]=[CH:6][CH:5]=[CH:22][CH:21]=2)=[CH:14][CH2:13]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 131727361(S)-2-(4'-methoxybiphen-4-yl) piperazine dihydrochloride

Product 1

HCID 131727363(S)-2-(3-(4-methoxybiphen-4-yl)piperazin-1-yl)-3-methyl-6-(4-pyridyl)pyrimidin-4-oneYield 96%

Procedure

To a suspension of (S)-2-(4′-methoxybiphen-4-yl)-piperazine dihydrochloride (237 mg, 0.694 mmol) in tetrahydrofuran (5 mL) was added triethylamine (0.40 mL, 2.9 mmol) and then 2-chloro-3-methyl-6-(4-pyridyl)-3H-pyrimidin-4-one (128 mg, 0.579 mmol) at room temperature. After stirring for 28 h, the resulting mixture was concentrated in vacuo. The residue was partitioned between dichloromethane and saturated sodium bicarbonate aqueous solution, and the organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting solid was washed with hot ethanol to afford (S)-2-(3-(4-methoxybiphen-4-yl)piperazin-1-yl)-3-methyl-6-(4-pyridyl)pyrimidin-4-one (252 mg, 96%), which was treated with 4 N hydrogen chloride in ethyl acetate to yield its dihydrochloride salt (252 mg) as pale yellow crystals.

Workup

  1. customat room temperature
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. customThe residue was partitioned between dichloromethane and saturated sodium bicarbonate aqueous solution
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. washThe resulting solid was washed with hot ethanol

Sources & evidence

ORD record
ord-42c7b84a31604c4091f55d88e4c69265
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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