Ammonia → 2,4-Diamino-5-methyl-6-(2,5-dimethoxybenzyl)-7-chloropyrido[2,3-d]pyrimidine

HRID 1032817Notes

Reaction equation

HRID 1032817 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH2:25])[C:5]2[C:11]([CH3:12])=[C:10]([CH2:13][C:14]3[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=3[O:22][CH3:23])[C:9](=O)[NH:8][C:6]=2[N:7]=1.C[N+](C)=C[Cl:29].[Cl-].S(Cl)(Cl)=O.N1C2C=CC=NC=2C=NC=1.N>C(Cl)(Cl)Cl.CN(C)C=O>[NH2:1][C:2]1[N:3]=[C:4]([NH2:25])[C:5]2[C:11]([CH3:12])=[C:10]([CH2:13][C:14]3[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=3[O:22][CH3:23])[C:9]([Cl:29])=[N:8][C:6]=2[N:7]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 77311Chloro-N,N-dimethylformiminium chloride2×HCID 125974832,4-Diamino-5-methyl-6-(2,5-dimethoxybenzyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidineHCID 17882607Pyrido(3,2-d)pyrimidine

Product 1

HCID 125974842,4-Diamino-5-methyl-6-(2,5-dimethoxybenzyl)-7-chloropyrido[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Procedure

2,4-Diamino-5-methyl-6-(2,5-dimethoxybenzyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine (8 g) was chlorinated by treatment with Vilsmeier reagent prepared by slowly adding thionyl chloride (28.6) in dry chloroform (25 ml) to a solution of dimethylformamide (17.5) in chloroform (100 ml) at 0°-5° C. The cold mixture of the pyridopyrimidine and Vilsmeier reagent was stirred, gradually allowed to reach ambient temperatures and then heated at reflux for 3 hours. It was then treated with ethanolic base (80 ml) maintaining the temperature at 25°-30° C. with cooling. The brown product formed was isolated, treated further with aqueous ammonia and then recrystallized from ethanol to give 2,4-diamino-5-methyl-6-(2,5-dimethoxybenzyl)-7-chloropyrido[2,3-d]pyrimidine, m.p. 193°-196° (dec.).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperaturemaintaining the temperature at 25°-30° C.
  4. temperaturewith cooling
  5. customThe brown product formed
  6. customwas isolated
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-fc8abb684b0c49ae856e9df633ee733f
Source dataset
uspto-grants-1990_09
Patent number
US04959474

Reaction notes

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