Dimethylformamide → HCID 69217713, compound

HRID 2221947Notes

Reaction equation

HRID 2221947 reaction equation
Cl[CH2:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[O:12][C:13]=2[CH3:14])=[C:5]([O:22][CH3:23])[CH:4]=1.[OH:24][C:25]1[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][N:28]=[C:27]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:26]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[C:11]1[O:12][C:13]([CH3:14])=[C:9]([CH2:8][O:7][C:6]2[CH:20]=[CH:21][C:3]([CH2:2][O:24][C:25]3[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][N:28]=[C:27]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[N:26]=3)=[CH:4][C:5]=2[O:22][CH3:23])[N:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 657593Ethyl 4-hydroxy-2-phenylpyrimidine-5-carboxylateHCID 223445974-(4-Chloromethyl-2-methoxyphenoxymethyl)-2-(2-furyl)-5-methyloxazole

Product 1

HCID 69217713HCID 69217713, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(4-chloromethyl-2-methoxyphenoxy)methyl-5-methyl-2-(2-furyl)-1,3-oxazole (2.25 g), ethyl 4-hydroxy-2-phenylpyrimidine-5-carboxylate (1.50 g), potassium carbonate (1.27 g) and N,N-dimethylformamide (50 mL) was stirred at 90° C. for 2 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with 0.2N aqueous sodium hydroxide solution and water, dried over anhydrous magnesium sulfate and concentrated. The obtained crystals were recrystallized from tetrahydrofuran-ethyl acetate to give ethyl 4-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-2-phenylpyrimidine-5-carboxylate as colorless prism crystals (2.50 g, yield 75%). melting point: 142-143° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with 0.2N aqueous sodium hydroxide solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe obtained crystals were recrystallized from tetrahydrofuran-ethyl acetate

Sources & evidence

ORD record
ord-8f6b8d6beec749738301e754c141231c
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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