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Water → N-butyl-N-ethyl-2,5-dimethyl-7-(2,4,6-trimethylphenyl)pyrrolo(2,3-d)pyrimidin-4-amine

HRID 1884344
Notes
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Reaction equation

HRID 1884344 reaction equation
Cl[C:2]1[C:3]2[C:11]([CH3:12])=[CH:10][N:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[CH2:22]([NH:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH3:23].O>CS(C)=O.Cl>[CH2:25]([N:24]([CH2:22][CH3:23])[C:2]1[C:3]2[C:11]([CH3:12])=[CH:10][N:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1)[CH2:26][CH2:27][CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 25914ButylethylamineHCID 107805364-Chloro-7-mesityl-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 5311055N-butyl-N-ethyl-2,5-dimethyl-7-(2,4,6-trimethylphenyl)pyrrolo(2,3-d)pyrimidin-4-amineYield 81.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalyst
HCID 679
Dimethyl Sulfoxide
Solvent

Procedure

A mixture of 4-chloro-2,5-dimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidine (1.000 g, 3.36 mmol) and N-ethylbutylamine (3.400 g, 33.60 mmol) in 5 ml of dimethylsulfoxide was heated to reflux for 1.5 hours. The mixture was cooled and treated with water and a few drops of 2 N HCl to pH 6.5 and extracted with ethyl acetate. The organic layer was separated, washed with dilute sodium bicarbonate, brine, and dried over sodium sulfate anhydrous and concentrated to dryness. The residue was purified through silica gel column chromatography to give 995 mg (81% yield) of the title compound as an oil. 1H NMR (CDCl3) δ 6 0.90 (t, 3H), 1.23(t, 3H), 1.35(m, 2H), 1.60-1.70(m, 2H), 1.92(s, 6H), 2.30(s, 3H), 2.40(s, 3H), 2.46(s, 3H), 3.58(t, 2H), 3.66(q, 2H), 6.55(s, 1H), 6.95(s, 2H) ppm. The corresponding hydrogen chloride salt was prepared as a white crystals after recrystallization from ethyl acetate. 1H NMR (D2O) δ 0.90(t, 3H), 1.34(m, 5H), 1.75(m, 2H), 1.90(s, 6H), 2.37(s, 3H), 2.48(s, 3H), 2.55(s, 3H), 3.80-3.94(m, 4H), 7.09(s, 2H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with dilute sodium bicarbonate, brine
  7. dry with materialdried over sodium sulfate anhydrous
  8. concentrationconcentrated to dryness
  9. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-e6d9822e2f094164ac06e033b3a6fe2d
Source dataset
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06765008B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes