Toluene → Ethyl 8-ethyl-5-oxo-2-(pyrrolidin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

HRID 1703950Notes

Reaction equation

HRID 1703950 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:20])[C:8]2[CH:13]=[N:12][C:11](OC)=[N:10][C:9]=2[N:16]([CH2:18][CH3:19])[CH:17]=1)=[O:5])[CH3:2].[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.C1(C)C=CC=CC=1>O>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:20])[C:8]2[CH:13]=[N:12][C:11]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:10][C:9]=2[N:16]([CH2:18][CH3:19])[CH:17]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 31268PyrrolidineHCID 88152Ethyl 8-ethyl-5,8-dihydro-2-methoxy-5-oxopyrido(2,3-d)pyrimidine-6-carboxylate

Product 1

HCID 118556Ethyl 8-ethyl-5-oxo-2-(pyrrolidin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.9 g of 6-ethoxycarbonyl-8-ethyl-2-methoxy-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine, 4.6 g. of pyrrolidine and 12 g of toluene are heated for 2 hours at 90° C. After cooling, 100 cm3 of water are added to the mixture. The precipitate is filtered off and washed with water. After drying, 5.5 g of 6-ethoxycarbonyl-8-ethyl-5-oxo-2-pyrrolidino-5,8-dihydro-pyrido[2,3-d]pyrimidine are obtained. After recrystallisation from ethanol, it melts at 202° C and is identical to the product described in the literature.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate is filtered off
  3. washwashed with water
  4. customAfter drying

Sources & evidence

ORD record
ord-936d9201c28c415090c30e81572033b2
Source dataset
uspto-grants-1978_11
Patent number
US04125720

Reaction notes

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