US 12,466,796 B2
Process for preparing 5-(fluoro-4-imino-3-methyl)-1-tosyl-3,4 dihydropyrimidine-(1H)-one and derivatives of the compound
Gal Suez, Beer Sheva (IL); Samaa Alasibi, Hura (IL); and Yaakov Mines, Beer Sheva (IL)
Assigned to ADAMA MAKHTESHIM LTD., Beer Sheva (IL)
Appl. No. 17/762,557
Filed by Adama Makhteshim Ltd., Beer Sheva (IL)
PCT Filed Sep. 23, 2020, PCT No. PCT/IB2020/058893
§ 371(c)(1), (2) Date Mar. 22, 2022,
PCT Pub. No. WO2021/059160, PCT Pub. Date Apr. 1, 2021.
Claims priority of provisional application 62/904,482, filed on Sep. 23, 2019.
Prior Publication US 2023/0143040 A1, May 11, 2023
Int. Cl. C07D 239/47 (2006.01); C07C 273/18 (2006.01)
CPC C07D 239/47 (2013.01) [C07C 273/1863 (2013.01)] 14 Claims
 
1. A process for preparing a compound having the formula (I):

OG Complex Work Unit Chemistry
wherein
R is alkyl or alkylaryl;
each of X1, X2, X3, X4 and X5 is, independently, H, alkyl, alkenyl, alkynyl, alkoxy, haloalkyl, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, alkoxycarbonyl, alkyl carbonyl, hydroxyalkyl, ester, a halogen, —SH, —OH, —NH2, —NO2, —CN or CF3;
Y is O or S;
and Z is a halogen,
comprising reacting an alkyl-urea or thiourea of the formula RNH(C═Y) NH2 with a trialkyl orthoformate in the presence of a cyanoacyl derivative having the formula R′C(O)CH2CN, wherein R′ is OH, O—R″ or S—R″, wherein R″ is alkyl, or with a cyanoacetaldehyde dialkyl acetal, under conditions sufficient to obtain the compound of formula (III),

OG Complex Work Unit Chemistry