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Water → 4-(4-(methylsulfonyl)phenyl)-N-(tetrahydro-2H-pyran-4-yl)-6-(trifluoromethyl)pyrimidin-2-amine

HRID 6696
Notes
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Reaction equation

HRID 6696 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH:8]=[C:7]([C:21]([F:24])([F:23])[F:22])[N:6]=1)(=O)=O.[O:25]1[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]1.O>CN1CCCC1=O>[CH3:20][S:17]([C:14]1[CH:15]=[CH:16][C:11]([C:9]2[CH:8]=[C:7]([C:21]([F:24])([F:23])[F:22])[N:6]=[C:5]([NH:31][CH:28]3[CH2:29][CH2:30][O:25][CH2:26][CH2:27]3)[N:10]=2)=[CH:12][CH:13]=1)(=[O:19])=[O:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 4192234-AminotetrahydropyranHCID 111764432-(Methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine

Product 1

HCID 98223574-(4-(methylsulfonyl)phenyl)-N-(tetrahydro-2H-pyran-4-yl)-6-(trifluoromethyl)pyrimidin-2-amineYield 40%

Reagents, catalysts & solvents 1

HCID 13387
N-methyl-2-pyrrolidone
Solvent

Procedure

To a solution of 2-(methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine (0.277 g, 0.73 mmol) in N-methylpyrrolidone (1.25 ml) was added tetrahydro-2H-pyran-4-amine (0.147 g, 2 eq.), the mixture was stirred for 1 hour and then water (1.25 ml) was added dropwise. This resulted in a precipitate being formed, which was collected by filtration, and dried in vacuo (0.258 g). This material was then purified by autopurification to give the title compound as a colourless solid (0.116 g, 40%).

Workup

  1. customThis resulted in a precipitate
  2. custombeing formed
  3. filtrationwhich was collected by filtration
  4. customdried in vacuo (0.258 g)
  5. customThis material was then purified by autopurification

Sources & evidence

ORD record
ord-17ed47ef835b4d92b99869f4520b7108
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07084148B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes