Triethylamine → 1-[2-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-pyrimidin-4-yl]-piperidin-4-ol

HRID 1161656Notes

Reaction equation

HRID 1161656 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[CH:10]=2)[N:5]=[C:4]([NH:18][CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:3]=1.[OH:26][CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(N(CC)CC)C>C(O)CCC>[Cl:17][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[N:7]=[C:2]([N:30]3[CH2:31][CH2:32][CH:27]([OH:26])[CH2:28][CH2:29]3)[CH:3]=[C:4]([NH:18][CH:19]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[N:5]=2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 586260766-chloro-N2-(3-chloro-4-methoxy-phenyl)-N4-cycloheptyl-pyrimidine-2,4-diamine

Product 1

HCID 115179471-[2-(3-Chloro-4-methoxy-phenylamino)-6-cycloheptylamino-pyrimidin-4-yl]-piperidin-4-olYield 23%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of compound 6-chloro-N2-(3-chloro-4-methoxy-phenyl)-N4-cycloheptyl-pyrimidine-2,4-diamine (0.15 g, 0.39 mmol) in 1-butanol (5 mL) was added 4-hydroxypiperidine (0.12 g, 1.18 mmol) at 25° C. with stirring. To this triethylamine (0.43 mL, 3.15 mmol) was added dropwise and the mixture was stirred at 25° C. for 30 minutes. This was heated and refluxed for 12 hours under nitrogen atmosphere. The mixture was concentrated under vacuum, diluted with cold water (30 mL) and extracted with ethyl acetate (2×30 mL). The organic layers were collected, combined, washed with brine (30 mL), dried over anhydrous sodium sulphate, and concentrated under vacuum to give the desired compound. Yield: 23%.

Workup

  1. stirringthe mixture was stirred at 25° C. for 30 minutes
  2. temperatureThis was heated
  3. temperaturerefluxed for 12 hours under nitrogen atmosphere
  4. concentrationThe mixture was concentrated under vacuum
  5. additiondiluted with cold water (30 mL)
  6. extractionextracted with ethyl acetate (2×30 mL)
  7. customThe organic layers were collected
  8. washwashed with brine (30 mL)
  9. dry with materialdried over anhydrous sodium sulphate
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4125346a469244118cf4c62cb459b437
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

Loading…