4-Piperidinol, 1-methyl- → 7-benzylsulfonyl-3-(2-chlorophenyl)-1-(1-methylpiperidin-4-yl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1280574Notes

Reaction equation

HRID 1280574 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([S:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:20])=[O:19])=[N:14][CH:15]=2)[NH:10][C:9]1=[O:28].C1(P(C2C=CC=CC=2)C2C=CC=CN=2)C=CC=CC=1.O[CH:49]1[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>O1CCCC1>[CH2:21]([S:18]([C:13]1[N:12]=[C:11]2[N:10]([CH:49]3[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]3)[C:9](=[O:28])[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH2:17][C:16]2=[CH:15][N:14]=1)(=[O:20])=[O:19])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 660484-Piperidinol, 1-methyl-HCID 6218932-PyridyldiphenylphosphineHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 180024743-(2-chlorophenyl)-7-benzylsulfonyl-3,4-dihydropyrimido[4,5-d]-pyrimidin-2(1H)-one

Product 1

HCID 184253927-benzylsulfonyl-3-(2-chlorophenyl)-1-(1-methylpiperidin-4-yl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneYield 28.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of sulfone 9.1 (1.0 g, 2.4 mmol), diphenyl-2-pyridylphosphine (1.9 g, 7.23 mmol) and 4-hydroxy-1-methylpiperidine (0.555 g, 4.8 mmol) was dissolved in anhydrous tetrahydrofuran under an atmosphere of nitrogen. To this solution was added di-tert-butylazodicarboxylate (1.67 g, 7.23 mmol) and the resulting mixture was stirred at room temperature for 2 hours, then concentrated in vacuo. The residue was purified by column chromatography on silica gel using 9:1 dichloromethane/methanol as eluant. The column fractions containing product were combined and concentrated in vacuo to give 354 mg of 7-benzylsulfonyl-3-(2-chlorophenyl)-1-(1-methylpiperidin-4-yl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography on silica gel using 9:1 dichloromethane/methanol as eluant
  3. additionThe column fractions containing product
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb3290d0909845fb9686e8d74077ab4e
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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