Potassium Carbonate → HCID 59411345, compound

HRID 1798855Notes

Reaction equation

HRID 1798855 reaction equation
[CH3:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:6](=[O:18])[NH:5][CH:4]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[C:3]=1[C:27]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)=[O:28].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:42][C:43]1[O:47][C:46]([C:48]([O:50][CH3:51])=[O:49])=[CH:45][CH:44]=1>CN(C)C=O.CO>[C:23]([C:22]1[CH:25]=[CH:26][C:19]([CH:4]2[N:5]([CH2:42][C:43]3[O:47][C:46]([C:48]([O:50][CH3:51])=[O:49])=[CH:45][CH:44]=3)[C:6](=[O:18])[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:17])[F:16])[CH:9]=3)[C:2]([CH3:1])=[C:3]2[C:27]([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)=[O:28])=[CH:20][CH:21]=1)#[N:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 75065Methyl 5-(chloromethyl)-2-furoateHCID 59411319HCID 59411319, compound

Product 1

HCID 59411345HCID 59411345, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of (4-{6-methyl-2-oxo-5-(pyridin-3-ylcarbonyl)-1-[3-(trifluoromethyl)-phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}benzonitrile (Example 21A) (1.00 mg, 0.22 mmol) and potassium carbonate (60 mg, 0.43 mmol) in dimethylformamide (3 ml) is added methyl 5-(chloromethyl)-2-furoate (57 mg, 0.32 mmol). The suspension is stirred at room temperature for 72 hours. The mixture is diluted with methanol (5 ml) and purified directly by preparative HPLC(RP18 column; eluent: acetonitrile/water 10:90→90:10).

Workup

  1. custompurified directly by preparative HPLC(RP18 column

Sources & evidence

ORD record
ord-cde4a85c35534790bc9130efcde3f924
Source dataset
uspto-grants-2013_01
Patent number
US08343987B2

Reaction notes

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