Sodium Hydroxide → 2-(4-Butoxyphenyl)-4-chloro-5-pyrimidinecarbonitrile

HRID 1833745Notes

Reaction equation

HRID 1833745 reaction equation
Cl.C(OC1C=CC(C(N)=N)=CC=1)CCC.C(OC(=O)C(=COCC)C#N)C.CC[O-].[Na+].[OH-].[Na+].[C:34]([C:36]1[C:37](O)=[N:38][C:39]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH2:49][CH2:50][CH2:51][CH3:52])=[CH:44][CH:43]=2)=[N:40][CH:41]=1)#[N:35].P(Cl)(Cl)([Cl:56])=O>C(O)C>[Cl:56][C:37]1[C:36]([C:34]#[N:35])=[CH:41][N:40]=[C:39]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH2:49][CH2:50][CH2:51][CH3:52])=[CH:44][CH:43]=2)[N:38]=1

Participants

8

Reactant 6

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 2723922Sodium ethoxideHCID 3015453Benzamidine, p-butoxy-, monohydrochlorideHCID 178450107HCID 178450107, compound

Product 1

HCID 22521972-(4-Butoxyphenyl)-4-chloro-5-pyrimidinecarbonitrile

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, 365 by reaction of p-n-butoxybenzamidine hydrochloride with α-ethoxymethylene-α -cyanoacetic acid ethyl ester and sodium ethylate in ethanol and then with sodium hydroxide solution. The resulting 5-cyano-4-hydroxy-2(4-n-butoxyphenyl)-pyrimidine (melting point 223.2°-229.5° C) is treated with phosphorus oxychloride to give 4-chloro-5-cyano-2-(4-n-butoxyphenyl)-pyrimidine having a melting point of 169.7°-170.2° C.

Workup

  1. customThe starting material can be obtained

Sources & evidence

ORD record
ord-aafd15d09dbb44e181eca534ed77e4d8
Source dataset
uspto-grants-1978_01
Patent number
US04066570

Reaction notes

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