1-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxyphenyl)-7-(methylsulfinyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one → 1-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-(2,3-dihydroxy-butylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 459976Notes

Reaction equation

HRID 459976 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][CH2:33][C@@H:34]([OH:38])[C@H:35]([OH:37])[CH3:36]>>[CH:1]1([N:6]2[C:11]3=[N:12][C:13]([NH:32][CH2:33][CH:34]([OH:38])[CH:35]([OH:37])[CH3:36])=[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 184448441-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxyphenyl)-7-(methylsulfinyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneHCID 55291132(2R,3R)-1-Aminobutane-2,3-diol

Product 1

HCID 103455801-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-(2,3-dihydroxy-butylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneYield 94%

Procedure

1-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-(2,3-dihydroxy-butylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared as described in Example 7 using 0.49 g (1.08 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 0.28 g (2.66 mmol) of (2R,3R)-1-amino-butane-2,3-diol. The crude product was purified using medium-pressure chromatography eluting with 20:1 dichloromethane/methanol to give 0.50 g (94%) of the title compound: mp 195° C.–196° C. (dec). MS (APCI) (m+1)/z 494.2.

Workup

  1. custom1-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-(2,3-dihydroxy-butylamino)-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-eb32b1c4f99b444f9afca163ff9ad7a5
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

Loading…