Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → (+/-)-5,8-Dihydro-4-methoxy-7-methyl-5-(3-nitrophenyl)pyrido[2,3-d]pyrimidine-6-carboxylic acid isopropyl ester

HRID 2118949

Reaction equation

HRID 2118949 reaction equation
[CH:1]([O:4][C:5]([C:7]1[CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:9]2[C:14](=[O:15])[NH:13][CH:12]=[N:11][C:10]=2[NH:16][C:17]=1[CH3:18])=[O:6])([CH3:3])[CH3:2].[CH3:28][O+](C)C.F[B-](F)(F)F>ClCCCl>[CH:1]([O:4][C:5]([C:7]1[CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:9]2[C:14]([O:15][CH3:28])=[N:13][CH:12]=[N:11][C:10]=2[NH:16][C:17]=1[CH3:18])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 136393698(+/-)-3,4,5,8-Tetrahydro-7-methyl-5-(3-nitrophenyl)-4-oxo-pyrido[2,3-d]-pyrimidine-6-carboxylic acid isopropyl ester

Product 1

HCID 13645046(+/-)-5,8-Dihydro-4-methoxy-7-methyl-5-(3-nitrophenyl)pyrido[2,3-d]pyrimidine-6-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Three and 0.7 g (10 mmol) (±)-3,4,5,8-tetrahydro-7-methyl-5-(3-nitrophenyl)-4-oxo-pyrido[2,3-d]-pyrimidine-6-carboxylic acid isopropyl ester and 3.0 g (20 mmol) trimethyloxonium-tetrafluoroborate are stirred in 150 ml 1,2-dichloroethane in nitrogen atmosphere and at room temperature for three hours. The product is extracted twice with 50 ml saturated sodium hydrogen carbonate solution, the organic phase is separated, dried over sodium sulfate and reduced under vacuum. Twice recrystallizing the residue from diisopropyl ether/isopropanol yields the product in the form of colorless crystals with a mp of 212°-213° C.

Workup

  1. extractionThe product is extracted twice with 50 ml saturated sodium hydrogen carbonate solution
  2. customthe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. customTwice recrystallizing the residue from diisopropyl ether/isopropanol
  5. customyields the product in the form of colorless crystals with a mp of 212°-213° C.

Sources & evidence

ORD record
ord-c07665dce31646e6b4ef70418170171f
Source dataset
uspto-grants-1987_07
Patent number
US04681882

Linked notes

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