1,4'-Bipiperidine → 7-(1,4'-bipiperidin-1'-yl)-5-chloro-1-(2,6-difluorophenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 2243724Notes

Reaction equation

HRID 2243724 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](S(C)=O)[N:5]=[C:4]2[N:11]([C:16]3[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=3[F:23])[C:12](=[O:15])[NH:13][CH2:14][C:3]=12.[N:24]1([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[N:24]1([CH:30]2[CH2:35][CH2:34][N:33]([C:6]3[N:5]=[C:4]4[N:11]([C:16]5[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=5[F:23])[C:12](=[O:15])[NH:13][CH2:14][C:3]4=[C:2]([Cl:1])[N:7]=3)[CH2:32][CH2:31]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 786071,4'-BipiperidineHCID 81531DiisopropylethylamineHCID 57530505HCID 57530505, compound

Product 1

HCID 575305197-(1,4'-bipiperidin-1'-yl)-5-chloro-1-(2,6-difluorophenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneYield 115%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-1-(2,6-difluorophenyl)-7-(methylsulfinyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (200 mg, 0.56 mmol) in DCM (10 mL) were added 1,4′-bipiperidine (270 mg, 1.61 mmol) and N,N-diisopropylethylamine (0.3 mL, 1.7 mmol). The resultant solution was stirred at room temperature over night. The result mixture was concentrated. CombiFlash chromatography (mobile phase DCM/DCM[90]+MeOH[7]+NH4OH[3]) provided the title compound as a white solid (298 mg, 83%). LC-MS m/z 463 (M+H)+.

Workup

  1. concentrationThe result mixture was concentrated

Sources & evidence

ORD record
ord-3eb3de291a884988a54eb022b3efc336
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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