3-(2,6-Difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one → 3-(2,6-Difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-(4-hydroxy-cyclohexylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 459975Notes

Reaction equation

HRID 459975 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[N:13]1[CH2:22][C:21]2[C:16](=[N:17][C:18](S(C)=O)=[N:19][CH:20]=2)[N:15]([CH2:26][CH3:27])[C:14]1=[O:28].[NH2:29][C@H:30]1[CH2:35][CH2:34][C@H:33]([OH:36])[CH2:32][CH2:31]1>>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[N:13]1[CH2:22][C:21]2[C:16](=[N:17][C:18]([NH:29][CH:30]3[CH2:35][CH2:34][CH:33]([OH:36])[CH2:32][CH2:31]3)=[N:19][CH:20]=2)[N:15]([CH2:26][CH3:27])[C:14]1=[O:28]

Participants

3

Reactant 2

HCID 184447943-(2,6-Difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneHCID 178511715HCID 178511715, compound

Product 1

HCID 100730853-(2,6-Difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-(4-hydroxy-cyclohexylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneYield 89.2%

Procedure

3-(2,6-Difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-(4-hydroxy-cyclohexylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared as described in Example 5 using 0.5 g (1.21 mmol) of 3-(2,6-difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 0.42 g (3.64 mmol) of trans-4-aminocyclohexanol. The crude product was purified using medium-pressure chromatography eluting with 20:1 dichloromethane/methanol to give 0.50 g (89%) of the title compound: mp 198° C.–202° C. MS (APCI) (m+1)/z 464.1.

Workup

  1. custom3-(2,6-Difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-(4-hydroxy-cyclohexylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared
  2. customThe crude product was purified
  3. washeluting with 20:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-7491e65235fb4f6cb5e96699acdfb697
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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