Potassium Carbonate → HCID 53889748, compound

HRID 344977Notes

Reaction equation

HRID 344977 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH2:22]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:22]([C:29]1[CH:30]=[CH:31][C:32]([C:33]([O:1][C:2]2[CH:7]=[N:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:10][CH:9]=3)=[N:4][CH:3]=2)=[O:34])=[CH:36][CH:37]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1708644-Heptylbenzoyl chlorideHCID 115293165-Hydroxy-2-(4-octylphenyl)pyrimidine

Product 1

HCID 53889748HCID 53889748, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.65 g of 5-methoxy-2-(4-n-octyl-phenyl)-pyrimidine [can be obtained by condensation of methyl β-hydroxy-α-methoxyacrylate with 4-n-octylbenzamidine hydrochloride, reaction of the 4-hydroxy-5-methoxypyrimidine obtained with P2S5 and reduction of the 4-mercaptopyrimidine obtained with a Raney nickel according to J. H. Chesterfield et al., J. Chem. Soc. 4590 (1960)] and 1.0 g of KOH in 15 ml of ethylene glycol are boiled for 10 hours. 10 ml of water are added to the cooled solution, which is then acidified using glacial acetic acid and extracted five times with ether. After conventional work-up, 5-hydroxy-2-(4-n-octylphenyl)-pyrimidine is obtained. (The other homologues can be obtained analogously). 0.26 g of the 5-hydroxy-2-(4-n-octylphenyl)pyrimidine obtained, 0.25 g of 4-n-heptylbenzoyl chloride and 0.15 g of potassium carbonate in 2.5 ml of dimethylformamide are subsequently heated at 100° C. for 12 hours with stirring. The salt is removed by filtration under suction, and the filtrate is concentrated to a residue, which is taken up in ether and washed with water until neutral. Conventional work-up gives 2-(4-n-octylphenyl)-pyrimidin-5-yl 4-n-heptylbenzoate.

Workup

  1. custom(The other homologues can be obtained analogously)
  2. customThe salt is removed by filtration under suction
  3. concentrationthe filtrate is concentrated to a residue, which
  4. washwashed with water until neutral

Sources & evidence

ORD record
ord-c3428873ed7e43539ed49718b928da04
Source dataset
uspto-grants-1991_10
Patent number
US05055221

Reaction notes

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