Serinol → 1-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-(2-hydroxy-1-hydroxymethyl-ethylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 459970Notes

Reaction equation

HRID 459970 reaction equation
[CH:1]1([N:6]2[C:11]3=[N:12][C:13](S(C)=O)=[N:14][CH:15]=[C:10]3[CH2:9][N:8]([C:19]3[C:24]([F:25])=[C:23]([O:26][CH3:27])[CH:22]=[C:21]([O:28][CH3:29])[C:20]=3[F:30])[C:7]2=[O:31])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:32][CH:33]([CH2:36][OH:37])[CH2:34][OH:35]>>[CH:1]1([N:6]2[C:11]3=[N:12][C:13]([NH:32][CH:33]([CH2:36][OH:37])[CH2:34][OH:35])=[N:14][CH:15]=[C:10]3[CH2:9][N:8]([C:19]3[C:24]([F:25])=[C:23]([O:26][CH3:27])[CH:22]=[C:21]([O:28][CH3:29])[C:20]=3[F:30])[C:7]2=[O:31])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 68294SerinolHCID 184448441-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxyphenyl)-7-(methylsulfinyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 100738381-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-(2-hydroxy-1-hydroxymethyl-ethylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneYield 72%

Procedure

1-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-(2-hydroxy-1-hydroxymethyl-ethylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared as described in Example 5 using 0.50 g (1.11 mmol) of 1-cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 0.30 g (3.32 mmol) of serinol. The crude product was purified using medium-pressure chromatography eluting with 20:1 dichloromethane/methanol to give 0.38 g (72%) of the title compound: mp 172° C.–174° C. MS (APCI) (m+1)/z 480.1.

Workup

  1. custom1-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-(2-hydroxy-1-hydroxymethyl-ethylamino)-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-30678240c57a429f8b90d30590d43a6c
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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