Dichloromethane → HCID 18619203, compound

HRID 1862282Notes

Reaction equation

HRID 1862282 reaction equation
N[C:2]1[C:3]([O:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])=[N:4][C:5]([O:8][C:9]2[CH:14]=[C:13]([N:15]3[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]3=[O:27])[C:12]([F:28])=[CH:11][C:10]=2[Cl:29])=[CH:6][CH:7]=1.COCCOC.ClCCl.N(OC(C)(C)C)=O>CCCCC>[Cl:29][C:10]1[CH:11]=[C:12]([F:28])[C:13]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]2=[O:27])=[CH:14][C:9]=1[O:8][C:5]1[CH:6]=[CH:7][CH:2]=[C:3]([O:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[N:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 80711,2-DimethoxyethaneHCID 10906Tert-Butyl nitriteHCID 18619232HCID 18619232, compound

Product 1

HCID 18619203HCID 18619203, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

0.72 g of boron trifluoride diethyl ether complex was added to a mixture of 1.28 g of 3-amino-6-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(methoxycarbonyl)methoxypyridine, 3 ml of 1,2-dimethoxyethane and 1 ml of dichloromethane dropwise at −7° C. The mixture was stirred for 10 minutes at the same temperature, then, to the reaction solution was added 0.31 g of t-butyl nitrite dropwise at −5° C. or lower. The mixture was stirred for 1 hour at the same temperature, then, into the mixture was poured n-pentane. The solvent was removed by decantation. 7 ml of ethanol, and 1.2 g of zinc (dust) was added to the residue, and it was stirred at reflux temperature for 1.5 hour. The reaction solution was filtrated through Celite, and the solvent was distilled off, then, the resulted residue was subjected to silica gel chromatography to obtain 0.73 g of 2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-6-(methoxycarbonyl)methoxypyridine [present compound 2-45].

Workup

  1. stirringThe mixture was stirred for 1 hour at the same temperature
  2. customThe solvent was removed by decantation
  3. addition7 ml of ethanol, and 1.2 g of zinc (dust) was added to the residue, and it
  4. stirringwas stirred
  5. temperatureat reflux temperature for 1.5 hour
  6. filtrationThe reaction solution was filtrated through Celite
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-d50213cc45aa42819e479190a8367177
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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