Sodium hydride → 3-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione

HRID 275658

Reaction equation

HRID 275658 reaction equation
C[Si](C)(C)[O-].[Na+].[NH2:7]/[C:8](/[C:15]([F:18])([F:17])[F:16])=[CH:9]\[C:10]([O:12]CC)=O.[NH2:19][C:20]1[C:21]([O:34][CH3:35])=[C:22]([NH:28][C:29](=O)[O:30]CC)[C:23]([F:27])=[CH:24][C:25]=1[Cl:26].C1CCN2C(=NCCC2)CC1.[H-].[Na+]>CN(C=O)C>[NH2:19][C:20]1[C:21]([O:34][CH3:35])=[C:22]([N:28]2[C:10](=[O:12])[CH:9]=[C:8]([C:15]([F:16])([F:17])[F:18])[NH:7][C:29]2=[O:30])[C:23]([F:27])=[CH:24][C:25]=1[Cl:26]

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 18315064ethyl N-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)carbamateHCID 23672319Sodium trimethylsilanolate2×

Product 1

HCID 183150803-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-b0d1e0b5359340c1aa863386b79bc1a2
Source dataset
uspto-grants-2002_03
Patent number
US06352958B1

Linked notes

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