Urea → 1-(3-Methylphenyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one

HRID 436416Notes

Reaction equation

HRID 436416 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2[C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:2]=1.N[C:18](N)=[O:19]>>[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:8]3[N:9]=[CH:10][CH:11]=[CH:12][C:13]=3[CH2:14][NH:15][C:18]2=[O:19])[CH:2]=1

Participants

3

Reactant 2

HCID 1176UreaHCID 21452450HCID 21452450, compound

Product 1

HCID 132593341-(3-Methylphenyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-oneYield 53.9%

Conditions

Temperature
180 °C

Procedure

To a mixture of 4.3 g 2-(m-toluidino)-3-aminomethylpyridine and 12 g of urea was heated at 180° C for 2 hours and further heated at 200° C for 30 minutes. After cooling, crude reaction product precipitated was collected by filtration and washed with sufficient amounts of warm water. This product was purified by recrystallization from methanol to give 2.6 g of 1-(m-tolyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine as colorless prisms, melting at 212° - 214° C.

Workup

  1. temperaturefurther heated at 200° C for 30 minutes
  2. temperatureAfter cooling
  3. customcrude reaction product
  4. customprecipitated
  5. filtrationwas collected by filtration
  6. washwashed with sufficient amounts of warm water
  7. customThis product was purified by recrystallization from methanol

Sources & evidence

ORD record
ord-0bc6a1ed3c6b4551b6bb5f4cc2e14fe4
Source dataset
uspto-grants-1977_02
Patent number
US04009166

Reaction notes

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