Potassium Carbonate → HCID 59411338, compound

HRID 1366261Notes

Reaction equation

HRID 1366261 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:44][CH:45]=[C:46]([C:48]([O:50][CH3:51])=[O:49])[N:47]=1>CN(C)C=O>[C:23]([C:22]1[CH:25]=[CH:26][C:19]([CH:4]2[N:5]([CH2:42][C:43]3[O:44][CH:45]=[C:46]([C:48]([O:50][CH3:51])=[O:49])[N:47]=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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2763199Methyl 2-(chloromethyl)oxazole-4-carboxylateHCID 59411319HCID 59411319, compound

Product 1

HCID 59411338HCID 59411338, compound

Reagents, catalysts & solvents 1

HCID 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) (100 mg, 0.22 mmol and potassium carbonate (60 mg, 0.43 mmol) in dimethylformamide (3 ml) is added methyl 2-(chloromethyl)-1,3-oxazole-4-carboxylate (57 mg, 0.32 mmol). The reaction mixture is stirred for 72 hours at room temperature. The crude product is quenched with water (20 ml) and extracted with ethyl acetate (3×50 ml). The combined organic phases are washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water 30:70→90:10).

Workup

  1. customThe crude product is quenched with water (20 ml)
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water 30:70→90:10)

Sources & evidence

ORD record
ord-ac6e04207ed84a5d86aca28dc6f43862
Source dataset
uspto-grants-2011_02
Patent number
US07893073B2

Reaction notes

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