Reaction #362840

ord-b0d1e0b5359340c1aa863386b79bc1a2

Reaction equation

C[Si](C)(C)[O-].[Na+]
sodium trimethylsilanolate
C[Si](C)(C)[O-].[Na+]
sodium trimethylsilanolate
CCOC(=O)Nc1c(F)cc(Cl)c(N)c1OC
ethyl N-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)carbamate
C1CCC2=NCCCN2CC1
DBU
C1CCC2=NCCCN2CC1
DBU
[H-].[Na+]
sodium hydride
CCOC(=O)/C=C(\N)C(F)(F)F
ethyl 3-amino4,4,4-trifluorocrotonate
→
COc1c(N)c(Cl)cc(F)c1-n1c(=O)cc(C(F)(F)F)[nH]c1=O
title compound
COc1c(N)c(Cl)cc(F)c1-n1c(=O)cc(C(F)(F)F)[nH]c1=O
3-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione

Reactants

C[Si](C)(C)[O-].[Na+]
sodium trimethylsilanolate
C[Si](C)(C)[O-].[Na+]
sodium trimethylsilanolate
CCOC(=O)Nc1c(F)cc(Cl)c(N)c1OC
ethyl N-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)carbamate
C1CCC2=NCCCN2CC1
DBU
C1CCC2=NCCCN2CC1
DBU
[H-].[Na+]
sodium hydride
CCOC(=O)/C=C(\N)C(F)(F)F
ethyl 3-amino4,4,4-trifluorocrotonate

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThis compound was prepared

Procedure

This compound was prepared using 4.0 grams (0.036 mole) of sodium trimethylsilanolate, 6.6 grams (0.036 mole) of ethyl 3-amino4,4,4-trifluorocrotonate, 8.5 grams (0.032 mole) of ethyl N-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)carbamate, and 2.2 grams (0.014 mole) of DBU in 75 mL of DMF. This preparation differs from well-known literature preparations for pyrimidinedione rings in that sodium trimethylsilanolate and DBU were used rather than sodium hydride. The yield of title compound was 1.7 grams. The NMR spectrum was consistent with the proposed structure.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06352958B1uspto-grants-2002_03