Pyridine → HCID 16221117, compound

HRID 1767111Notes

Reaction equation

HRID 1767111 reaction equation
[CH3:1][C:2]([OH:4])=[O:3].O[C:6]1[N:11]=[CH:10][N:9]=[C:8]([OH:12])[CH:7]=1.C[C:14]1[CH:21]=[CH:20][C:17]([C:18]#N)=[CH:16][CH:15]=1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C[CH2:38][O:39][C:40](C)=[O:41]>ClCCl>[C:2]([O:4][C:7]1[C:6]([C:40]([O:39][CH3:38])=[O:41])=[N:11][C:10]([C:14]2[CH:15]=[CH:16][C:17]([CH3:18])=[CH:20][CH:21]=2)=[N:9][C:8]=1[O:12][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:3])[C:1]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 7724p-TolunitrileHCID 8857Ethyl AcetateHCID 178476733HCID 178476733, compound

Product 1

HCID 16221117HCID 16221117, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of dihydroxypyrimidine methylcarboxylate (B-1) (prepared from 4-methylbenzonitrile by procedures similar to those set forth in Scheme A), 4 eq. of benzoylchloride and 8 eq. of dry pyridine was stirred in dry dichloromethane at room temperature over night. The reaction mixture was diluted with EtOAc and the organic layer was washed twice with 1N HCl, once with brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The solid residue was triturated with diethyl ether to give product (B-2).

Workup

  1. washthe organic layer was washed twice with 1N HCl, once with brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe solid residue was triturated with diethyl ether
  6. customto give product (B-2)

Sources & evidence

ORD record
ord-69e163cc37bb444a8632a79d43d6dd98
Source dataset
uspto-grants-2007_06
Patent number
US07232819B2

Reaction notes

Loading…