Methyl iodide → 4-(3-Chloro-4-methoxybenzylamino)-5-methoxycarbonyl-2,6-dichloropyrimidine

HRID 917643Notes

Reaction equation

HRID 917643 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:5][NH:6][C:7]1[C:12]([C:13]([OH:15])=[O:14])=[C:11]([Cl:16])[N:10]=[C:9]([Cl:17])[N:8]=1.[C:23](=O)([O-])O.[Na+].CI.C(OC(C)C)(C)C>C(Cl)Cl.CCCCCC.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH3:23])=[O:14])=[C:11]([Cl:16])[N:10]=[C:9]([Cl:17])[N:8]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 7914Diisopropyl EtherHCID 516892Sodium Bicarbonate2×HCID 178482874-(3-Chloro-4-methoxybenzylamino)-5-carboxy-2,6-dichloropyrimidine

Product 1

HCID 178483594-(3-Chloro-4-methoxybenzylamino)-5-methoxycarbonyl-2,6-dichloropyrimidine

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A mixture of 4-(3-chloro-4-methoxybenzylamino)-5-carboxy-2,6-dichloropyrimidine (prepared in the above (1)) 17.55 g, sodium hydrogen carbonate 4.07 g, methyl iodide 5.48 ml and dimethylformamide 50 ml is stirred overnight at room temperature. The reaction mixture is diluted an aqueous saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo to give a pale yellow solid. The solid is suspended in a mixture of methylene chloride, isopropyl ether and hexane, and filtered. The precipitate is washed with a mixture of isopropyl ether and hexane to give 4-(3-chloro-4-methoxybenzylamino)-5-methoxycarbonyl-2,6-dichloropyrimidine as a colorless crystalline powder 8.64 g. mp 118-119° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customto give a pale yellow solid
  6. filtrationfiltered
  7. washThe precipitate is washed with a mixture of isopropyl ether and hexane

Sources & evidence

ORD record
ord-0fb457c0d543483fa84c27b7ce87fa68
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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