Hydrochloric Acid → HCID 53787511, compound

HRID 258231Notes

Reaction equation

HRID 258231 reaction equation
[CH:1]([O:4][C:5](=[O:24])[C:6]1[CH:11]=[C:10]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([CH3:19])[N:14]([CH3:20])[C:13]2=[O:21])[C:9]([F:22])=[CH:8][C:7]=1Cl)([CH3:3])[CH3:2].[Cu][C:26]#[N:27].C(OCC)(=O)C.Cl>CN1CCCN(C)C1=O.O>[CH:1]([O:4][C:5](=[O:24])[C:6]1[CH:11]=[C:10]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([CH3:19])[N:14]([CH3:20])[C:13]2=[O:21])[C:9]([F:22])=[CH:8][C:7]=1[C:26]#[N:27])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 19832675HCID 19832675, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 53787511HCID 53787511, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
195 °C

Procedure

A mixture of 50.0 g of 2-chloro-5-[3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-4-fluorobenzoic acid isopropyl ester and 25.4 g of copper(I) cyanide in 225 ml of dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is heated for 2.5 hours at 195° C. under nitrogen. The mixture is then cooled to room temperature and 2 l of ethyl acetate are added. The mixture is then poured onto 1.31 of water and 300 ml of 32% hydrochloric acid, and the whole is stirred for 45 minutes at room temperature until two distinct layers have formed. The organic phase is removed, washed twice with 200 ml of water each time and dried over anhydrous sodium sulfate. Concentration by evaporation of the organic solution yields crystalline 2-cyano-5-[3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-4-fluorobenzoic acid isopropyl ester, m.p. 188°-200° C.

Workup

  1. temperatureThe mixture is then cooled to room temperature
  2. customhave formed
  3. customThe organic phase is removed
  4. washwashed twice with 200 ml of water each time
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationConcentration
  7. customby evaporation of the organic solution

Sources & evidence

ORD record
ord-5a401d4388e641649bf795dbcb926689
Source dataset
uspto-grants-1993_11
Patent number
US05266554

Reaction notes

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