1,4-Dioxane → HCID 19014324, compound

HRID 1728549Notes

Reaction equation

HRID 1728549 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:17][CH3:18])[C:5]2[CH:10]=[CH:9][N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.O1CCOC[CH2:20]1>>[CH3:1][C:2]1[N:3]([CH3:20])[C:4](=[N:17][CH3:18])[C:5]2[CH:10]=[CH:9][N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 19014333N,2-Dimethyl-7-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 19014324HCID 19014324, compound

Procedure

A mixture of 2-methyl-4-methylamino-7-phenyl-7H-pyrrolo-[2,3-d] pyrimidine (0.5g, 2.1mM) and dioxan (15ml) was heated under reflux for 18 hours. The mixture was cooled and then the solvent was removed by evaporation. The residue was purified by flash chromatography on ICN neutral alumina (32-63) using methylene chloride which contained an increasing amount of methanol (up to a maximum of 5%) as eluant to give a solid. This solid was recrystallised from hexane to give 2,3-dimethyl-4-methylimino-7-phenyl-3H,7H-pyrrolo[2,3-d] pyrimidine as a white solid (126mg), m p. 160-161° C; microanalysis, found: C, 71 2; H,5 9; N,22.0%; C14H14N4 requires C,71.4; H, 6.3; N, 22.2%; NMR: 2.48(3H,s,C-CH3), 3.48 (3H,s,N-CH3), 3.56(3H,s,N-CH3), 6.90(1H,d,CH), 6.97(1H,d,CH), 7.34(1H, complex, aromatic), 7.47(2H, complex, aromatic), 7.60(1H, complex, aromatic).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed by evaporation
  5. customThe residue was purified by flash chromatography on ICN neutral alumina (32-63)
  6. customto give a solid
  7. customThis solid was recrystallised from hexane

Sources & evidence

ORD record
ord-9b22da2a913e436a8f35130a03a09de6
Source dataset
uspto-grants-1994_07
Patent number
US05328910

Reaction notes

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