Methyl cyanoacetate → 3-[4-Chloro-3-(2-cyano-2-methoxycarbonylethenyl)-phenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

HRID 1978847Notes

Reaction equation

HRID 1978847 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].N1CCCCC1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:26](=[O:27])[CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[N:23]([CH3:32])[C:22]2=[O:33])=[CH:17][C:16]=1[CH:34]=O.C(OC(C)C)(C)C>O1CCCC1>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:26](=[O:27])[CH:25]=[C:24]([C:28]([F:29])([F:31])[F:30])[N:23]([CH3:32])[C:22]2=[O:33])=[CH:17][C:16]=1[CH:34]=[C:3]([C:1]#[N:2])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 7747Methyl cyanoacetate2×HCID 7914Diisopropyl EtherHCID 8082PiperidineHCID 212012252-Chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]benzaldehyde

Product 1

HCID 702315503-[4-Chloro-3-(2-cyano-2-methoxycarbonylethenyl)-phenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.97 ml of methyl cyanoacetate and 0.3 ml of piperidine were added to a solution of 3.3 g of 3-(4-chloro-3-formylphenyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine in 100 ml of tetrahydrofuran. After the mixture had been stirred for 5 hours at the reflux temperature, a further 0.97 ml of methyl cyanoacetate was added and refluxing was continued for a further 5 hours. The reaction mixture was evaporated down and the oil obtained was chromatographed (dichloromethane). The solid obtained was stirred with diisopropyl ether, isolated, washed with petroleum ether and dried.

Workup

  1. temperaturerefluxing
  2. waitwas continued for a further 5 hours
  3. customThe reaction mixture was evaporated down
  4. customthe oil obtained
  5. customwas chromatographed (dichloromethane)
  6. customThe solid obtained
  7. customisolated
  8. washwashed with petroleum ether
  9. customdried

Sources & evidence

ORD record
ord-b260a0c6652f4a8e927ce82c98368a03
Source dataset
uspto-grants-2001_05
Patent number
US06239074B1

Reaction notes

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