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

HRID 530084Notes

Reaction equation

HRID 530084 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+].[CH3:22][CH:23]([NH2:25])[CH3:24].O>C(O)CCC>[CH2:1]([NH:4][C:5]1[N:6]=[C:7]([NH:25][CH:23]([CH3:24])[CH3:22])[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 6363IsopropylamineHCID 11430Potassium CarbonateHCID 735546474-Chloro-7-methyl-N-propyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Product 1

HCID 677740072-(n-Propyl)amino-4-(i-propyl)amino-7-methyl-pyrrolo[2,3-d]pyrimidineYield 75%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 2-(n-propyl)amino-4-chloro-7-methyl-pyrrolo[2,3-d]pyrimidine (1.6 g, 7.1 mmol) in n-butanol (10 mL) was added potassium carbonate (4.9 g, 35.5 mmol), followed by propan-2-amine (632 mg, 10.7 mmol). The mixture was stirred in an autoclave equipped with a stirrer at 140° 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 lastly dried over anhydrous Na2SO4. The volatiles were removed in vacuo and the residue was purified by flash column chromatography (PE/EtOAc=3/1) to yield 2-(n-propyl)amino-4-(i-propyl)amino-7-methyl-pyrrolo[2,3-d]pyrimidine (1.2 g, 75%) as a yellow solid. LCMS: (ESI) m/z=248 (M+H)+.

Workup

  1. customequipped with a stirrer at 140° 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 lastly dried over anhydrous Na2SO4
  5. customThe volatiles were removed in vacuo
  6. customthe residue was purified by flash column chromatography (PE/EtOAc=3/1)

Sources & evidence

ORD record
ord-af872d9c325a481aafcec9d8117c49de
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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