2-(4-Hydroxyphenyl)-5-octylpyrimidine → p-(5-n-Octylpyrimidin-2-yl)-phenyl (S,S)-3-methyl-2-chloropentanoate

HRID 274204Notes

Reaction equation

HRID 274204 reaction equation
[CH3:1][C@@H:2]([CH2:8][CH3:9])[C@H:3]([Cl:7])[C:4]([OH:6])=[O:5].[CH2:10]([C:18]1[CH:19]=[N:20][C:21]([C:24]2[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=2)=[N:22][CH:23]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>ClCCl>[CH3:1][C@@H:2]([CH2:8][CH3:9])[C@H:3]([Cl:7])[C:4]([O:6][C:27]1[CH:26]=[CH:25][C:24]([C:21]2[N:20]=[CH:19][C:18]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:23][N:22]=2)=[CH:29][CH:28]=1)=[O:5]

Participants

4

Reactant 2

HCID 6040552-(4-Hydroxyphenyl)-5-octylpyrimidineHCID 11051847(2S,3S)-2-Chloro-3-methylvaleric Acid

Product 1

HCID 14121127p-(5-n-Octylpyrimidin-2-yl)-phenyl (S,S)-3-methyl-2-chloropentanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8 g of (S,S)-3-methyl-2-chloropentanoic acid, 16 g of p-(5-n-octylpyrimidin-2-yl)phenol, 11.6 g of N,N-dicyclohexylcarbodiimide, 0.6 g of 4-N,N-dimethylamino-pyridine and 300 ml of dichloromethane is stirred overnight at room temperature. After filtering off the precipitated urea derivative, the filtrate is washed with dilute hydrochloric acid and water, and the organic phase is worked up in the usual manner. p-(5-n-Octylpyrimidin-2-yl)-phenyl (S,S)-3-methyl-2-chloropentanoate is obtained.

Workup

  1. filtrationAfter filtering off the precipitated urea derivative
  2. washthe filtrate is washed with dilute hydrochloric acid and water

Sources & evidence

ORD record
ord-c17fdc90c5bd491e92b65da11f2d850c
Source dataset
uspto-grants-1995_02
Patent number
US05389290

Reaction notes

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