HCID 18425515, compound → HCID 178517126, compound

HRID 1280565Notes

Reaction equation

HRID 1280565 reaction equation
C(S([C:11]1[N:16]=[C:15]2[N:17]([CH2:29][C:30]([F:33])([F:32])[F:31])[C:18](=[O:28])[N:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[CH2:20][C:14]2=[CH:13][N:12]=1)(=O)=O)C1C=CC=CC=1.[NH2:34][C@H:35]1[CH2:40][CH2:39][C@H:38]([OH:41])[CH2:37][CH2:36]1>CN1CCCC1=O>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:19]1[CH2:20][C:14]2[C:15](=[N:16][C:11]([NH:34][C@H:35]3[CH2:40][CH2:39][C@H:38]([OH:41])[CH2:37][CH2:36]3)=[N:12][CH:13]=2)[N:17]([CH2:29][C:30]([F:32])([F:31])[F:33])[C:18]1=[O:28]

Participants

4

Reactant 2

HCID 18425515HCID 18425515, compoundHCID 178511715HCID 178511715, compound

Product 1

HCID 178517126HCID 178517126, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

7-Benzylsulfonyl-3-(2-chlorophenyl)-1-(2,2,2-trifluoroethyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (300 mg, 0.604 mmol), trans-4-aminocyclohexanol (208 mg, 3 equivalents) and 1-methyl-2-pyrrolidinone (0.3 mL) were heated with stirring at 110° C. for 20 minutes, at which time it was cooled to room temperature. The residue was purified using preparative thin layer chromatography using ethyl acetate as eluant, to give 155 mg of 3-(2-chlorophenyl)-7-(trans4-hydroxycyclohexylamino)-1-(2,2,2-trifluoroethyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as an off-white powder.

Workup

  1. temperaturewas cooled to room temperature
  2. customThe residue was purified

Sources & evidence

ORD record
ord-e11d7fdc8fd247f7a703d878f750d4c4
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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