Water → HCID 66601916, compound

HRID 707604Notes

Reaction equation

HRID 707604 reaction equation
[Si]([O:8][CH2:9][CH2:10][S:11]([C:14]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=1[CH:22]1[C:27]([C:28]#[N:29])=[C:26]([CH3:30])[N:25]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=2)[C:24](=[O:41])[NH:23]1)(=[O:13])=[O:12])(C(C)(C)C)(C)C.FC(F)(F)C(O)=O.C(#N)C.O>ClCCl>[C:20]([C:18]1[CH:17]=[CH:16][C:15]([CH:22]2[C:27]([C:28]#[N:29])=[C:26]([CH3:30])[N:25]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:39])[F:40])[CH:32]=3)[C:24](=[O:41])[NH:23]2)=[C:14]([S:11]([CH2:10][CH2:9][OH:8])(=[O:13])=[O:12])[CH:19]=1)#[N:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 66602141HCID 66602141, compound

Product 1

HCID 66601916HCID 66601916, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction was carried out under argon. 4-{2-[(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)sulfonyl]-4-cyanophenyl}-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (550 mg, 0.909 mmol) was initially charged in dichloromethane (30 ml), trifluoroacetic acid (30 ml) was added and the mixture was stirred at RT for 5 h (HPLC control). The mixture was then concentrated without heating, and the residue was taken up in dichloromethane (200 ml). The organic phase was washed with saturated sodium bicarbonate solution (2×50 ml) and with saturated sodium chloride solution (50 ml), dried over solid sodium sulfate, filtered and concentrated under reduced pressure. The oil obtained was taken up in a little acetonitrile, water was added and the mixture was lyophilized. The title compound was obtained as a solid (450 mg, quant.).

Workup

  1. concentrationThe mixture was then concentrated
  2. temperaturewithout heating
  3. washThe organic phase was washed with saturated sodium bicarbonate solution (2×50 ml) and with saturated sodium chloride solution (50 ml)
  4. dry with materialdried over solid sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe oil obtained
  8. additionwas added

Sources & evidence

ORD record
ord-c9f032c890ff4b60ba1e5aa831ec4991
Source dataset
uspto-grants-2015_11
Patent number
US09174997B2

Reaction notes

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