HCID 18445054, compound → HCID 10456178, compound

HRID 459989Notes

Reaction equation

HRID 459989 reaction equation
[CH2:1]([N:3]1[C:8]2=[N:9][C:10](S(C)=O)=[N:11][CH:12]=[C:7]2[CH2:6][N:5]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[C:17]=2[F:26])[C:4]1=[O:27])[CH3:2].[NH2:28][C@H:29]1[CH2:34][CH2:33][C@H:32]([OH:35])[CH2:31][CH2:30]1>O1CCOCC1>[CH2:1]([N:3]1[C:8]2=[N:9][C:10]([NH:28][CH:29]3[CH2:34][CH2:33][CH:32]([OH:35])[CH2:31][CH2:30]3)=[N:11][CH:12]=[C:7]2[CH2:6][N:5]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[C:17]=2[F:26])[C:4]1=[O:27])[CH3:2]

Participants

4

Reactant 2

HCID 18445054HCID 18445054, compoundHCID 178511715HCID 178511715, compound

Product 1

HCID 10456178HCID 10456178, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A flask was charged with 0.312 g (0.79 mmol) of 1-Ethyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one, 15 mL dioxane, and 0.273 g (2.37 mmol) of trans-4-Aminocyclohexanol, and the mixture was heated 48 hours at 95° C. The dioxane was removed under reduced pressure, and the crude residue was purified directly via column chromatography (20:1 dichloromethane/methanol). This procedure gave 0.215 g (66%) of 1-Ethyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-(4-hydroxy-cyclohexylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a white solid: mp=198° C.–204° C.; MS (APCI) m+1/z 462.

Workup

  1. customThe dioxane was removed under reduced pressure
  2. customthe crude residue was purified directly via column chromatography (20:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-834575af8a074bd0ab5ae850171217f6
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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