Cesium carbonate → HCID 136390991, compound

HRID 1616145Notes

Reaction equation

HRID 1616145 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].CC(C)([O-])C.[K+].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:25][C:26]1[NH:35][C:34](=[O:36])[C:33]2[C:28](=[CH:29][C:30]([C:37]([O:39][CH3:40])=[O:38])=[CH:31][CH:32]=2)[N:27]=1>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[O:36]=[C:34]1[C:33]2[C:28](=[CH:29][C:30]([C:37]([O:39][CH3:40])=[O:38])=[CH:31][CH:32]=2)[N:27]=[C:26]([CH2:25][O:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:10])([F:11])[F:1])[NH:35]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 679582-TrifluoromethylphenolHCID 23665647Potassium tert-butoxideHCID 135520070methyl 2-(chloromethyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate

Product 1

HCID 136390991HCID 136390991, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(trifluoromethyl)phenol (36 mg, 0.22 mmol) in THF (1 mL) was added potassium tert-butoxide (24 mg, 0.22 mmol) and the reaction was stirred at rt for 3 h. Then tetra-n-butylammonium iodide (9 mg, 0.024 mmol), cesium carbonate (78 mg, 0.24 mmol) and methyl 2-(chloromethyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate (30 mg, 0.12 mmol) in DMF (1 mL) was added. The reaction mixture was stirred at rt for 2 d. The mixture was then concentrated to afford methyl 4-oxo-2-{[2-(trifluoromethyl)phenoxy]methyl}-3,4-dihydroquinazoline-7-carboxylate. LC-MS: (FA) ES+379.

Workup

  1. stirringThe reaction mixture was stirred at rt for 2 d
  2. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-e6a2424603db419a97cd0b3fe4b35934
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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