Diethyl (ethoxymethylene)malonate → 2-(4-Pentylphenyl)pyrimidine-5-carbonitrile

HRID 1973593Notes

Reaction equation

HRID 1973593 reaction equation
Cl.[CH2:2]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=O)=[CH:9][CH:8]=1)[CH2:3][CH2:4][CH2:5][CH3:6].C(OC(=O)C(=COCC)C(OCC)=O)C.CC[O-].[Na+].C(O[C:38]([C:40]1[C:41](O)=[N:42]C(C2C=CC(CCCCC)=CC=2)=[N:44][CH:45]=1)=O)C.P(Cl)(Cl)(Cl)=O.C(OC(C1C(Cl)=NC(C2C=CC(CCCCC)=CC=2)=NC=1)=O)C>C(O)C>[C:45]([C:40]1[CH:38]=[N:13][C:11]([C:10]2[CH:14]=[CH:15][C:7]([CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:8][CH:9]=2)=[N:42][CH:41]=1)#[N:44]

Participants

8

Reactant 6

HCID 6871Diethyl (ethoxymethylene)malonateHCID 24813Phosphorus oxychlorideHCID 2723922Sodium ethoxideHCID 21388870HCID 21388870, compoundHCID 54263893HCID 54263893, compoundHCID 178442098HCID 178442098, compound

Product 1

HCID 135748242-(4-Pentylphenyl)pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material can be obtained according to the procedure of A. R. Todd and F. Bergel, J. Chem. Soc. 1937, 366 from p-n-pentylbenzamide hydrochloride and ethoxymethylenemalonic acid diethyl ester with sodium ethylate in ethanol and subsequent treatment of the obtained 2-(p-n-pentylphenyl)-4-hydroxy-5-pyrimidinecarboxylic acid ethyl ester (melting point 193.9°-194.4° C) with phosphorus oxychloride. The melting point of 2-(p-n-pentylphenyl)-4-chloro-5-pyrimidinecarboxylic acid ethyl ester is 58.5°-59.2° C.

Workup

  1. customThe starting material can be obtained
  2. customis 58.5°-59.2° C.

Sources & evidence

ORD record
ord-9cfb01f011174072b05c2b607a312d4c
Source dataset
uspto-grants-1976_12
Patent number
US03997536

Reaction notes

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