Water → 2-(n-Propyl)amino-4-dimethylamino-7-methyl-pyrrolo[2,3-d]pyrimidine

HRID 530085Notes

Reaction equation

HRID 530085 reaction equation
[CH2:1]([NH:4][C:5]1[N:6]=[C:7](Cl)[C:8]2[CH:13]=[CH:12][N:11]([CH3:14])[C:9]=2[N:10]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:23][NH:24][CH3:25].O>C(O)CCC>[CH2:1]([NH:4][C:5]1[N:6]=[C:7]([N:24]([CH3:25])[CH3:23])[C:8]2[CH:13]=[CH:12][N:11]([CH3:14])[C:9]=2[N:10]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 735546474-Chloro-7-methyl-N-propyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Product 1

HCID 677752072-(n-Propyl)amino-4-dimethylamino-7-methyl-pyrrolo[2,3-d]pyrimidineYield 76%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To 2-(n-propyl)amino-4-chloro-7-methyl-pyrrolo[2,3-d]pyrimidine (1.0 g, 4.5 mmol) (CXXIV) in n-butanol (20 mL) was added potassium carbonate (3.7 g, 27 mmol) and dimethylamine hydrochloride (1.0 g (22 mmol). The mixture was stirred in an autoclave equipped with a stirrer at 120° C. for 16 h. After cooling to room temperature, water was added (20 mL), and the mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with water and then with a brine solution, and dried over anhydrous Na2SO4. The solvents were removed in vacuo and the residue was purified by flash column chromatography (PE/EtOAc=6/1) to yield 2-(n-propyl)amino-4-dimethylamino-7-methyl-pyrrolo[2,3-d]pyrimidine (CXXVII, 800 mg, 76%) as a yellow solid. LCMS (ESI) m/z=234 (M+H)+.

Workup

  1. customequipped with a stirrer at 120° C. for 16 h
  2. extractionthe mixture was extracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialwith a brine solution, and dried over anhydrous Na2SO4
  5. customThe solvents were removed in vacuo
  6. customthe residue was purified by flash column chromatography (PE/EtOAc=6/1)

Sources & evidence

ORD record
ord-fe974b53695e420fb6d0eee6b6d6b54d
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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