1-Butanol → 2-(n-Propyl)amino-4-(4-hydroxypiperidin-1-yl)-7-methyl-pyrrolo[2,3-d]pyrimidine

HRID 1752154Notes

Reaction equation

HRID 1752154 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)CCC.C(=O)([O-])[O-].[K+].[K+].Cl.[NH:28]1[CH2:33][CH2:32][CH:31]([OH:34])[CH2:30][CH2:29]1>O>[CH2:1]([NH:4][C:5]1[N:6]=[C:7]([N:28]2[CH2:33][CH2:32][CH:31]([OH:34])[CH2:30][CH2:29]2)[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 2631-ButanolHCID 11430Potassium CarbonateHCID 162124994-Hydroxypiperidinium chlorideHCID 735546474-Chloro-7-methyl-N-propyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Product 1

HCID 677751392-(n-Propyl)amino-4-(4-hydroxypiperidin-1-yl)-7-methyl-pyrrolo[2,3-d]pyrimidineYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(n-Propyl)amino-4-chloro-7-methyl-pyrrolo[2,3-d]pyrimidine (CXXIV) (1.6 g, 7.1 mmol) was added to n-butanol (10 mL) followed by potassium carbonate (4.9 g, 35.5 mmol) and piperidin-4-ol hydrochloride (632 mg, 10.7 mmol). The mixture was stirred in an autoclave equipped with a stirrer at 130° 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 (pet ether/EtOAc=3/1) to yield 2-(n-propyl)amino-4-(4-hydroxypiperidin-1-yl)-7-methyl-pyrrolo[2,3-d]pyrimidine (1.2 g, 75%) as a yellow solid. LCMS (ESI) m/z=290 (M+H)+.

Workup

  1. customequipped with a stirrer at 130° 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 (pet ether/EtOAc=3/1)

Sources & evidence

ORD record
ord-0787699c4ea747a38b3f2c8a2f366ce4
Source dataset
uspto-grants-2015_10
Patent number
US09162992B2

Reaction notes

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