Methanol → HCID 86723894, compound

HRID 576786Notes

Reaction equation

HRID 576786 reaction equation
[OH:1][CH2:2][C@H:3]([N:5]1[C:10](=[O:11])[C:9]([C:12]2[N:16]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[N:15]=[CH:14][CH:13]=2)=[CH:8][N:7]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[C:6]1=[O:35])[CH3:4].F[C:37](F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(N(CC)C(C)C)(C)C.CO>ClCCl>[CH3:37][O:1][CH2:2][C@H:3]([N:5]1[C:10](=[O:11])[C:9]([C:12]2[N:16]([C:17]3[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=3)[N:15]=[CH:14][CH:13]=2)=[CH:8][N:7]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:34])[F:32])[CH:26]=2)[C:6]1=[O:35])[CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 86723895HCID 86723895, compound

Product 1

HCID 86723894HCID 86723894, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-4-(5-(3-(1-hydroxypropan-2-yl)-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (prepared in Example 111) (95.1 mg) in dichloromethane (1.0 ml) were added under ice-cooling trifluoromethanesulfonic anhydride (50.2 μl) and N,N-diisopropylethylamine (70.2 μl) and the resulting mixture was stirred under ice-cooling for one hour. To the reaction mixture was added methanol (5 ml) and the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford (R)-4-(5-(3-(1-methoxypropan-2-yl)-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (51.0 mg) as pale yellow solid.

Workup

  1. temperaturecooling for one hour
  2. stirringthe mixture was stirred at room temperature for one hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8dc3dab14aad4b36a5b614e44020b2db
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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