4,6-Dichloropyrimidine → tert-Butyl 3-((6-chloropyrimidin-4-yl)amino)piperidine-1-carboxylate

HRID 404802Notes

Reaction equation

HRID 404802 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:7]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 5458091-BOC-3-Aminopiperidine

Product 1

HCID 22309474tert-Butyl 3-((6-chloropyrimidin-4-yl)amino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4,6-dichloropyrimidine (0.1 g, 0.671 mmol), 3-amino-Boc-piperidine (0.16 g, 0.80 mmol) and DIPEA (0.086 g, 6.71 mmol) in n-butanol (5.0 mL) was heated in a pressure tube (120° C., 12 h). The solution was cooled, was quenched with water (2 mL) and was extracted with EtOAc (2×15 mL). The combined EtOAc extract was washed with water (5 mL), brine (5 mL), was dried over Na2SO4 and was concentrated under reduced pressure to give tert-butyl 3-(6-chloropyrimidin-4-ylamino)piperidine-1-carboxylate, which was dried under high vacuum and was used as such for next step without further purification.

Workup

  1. temperatureThe solution was cooled
  2. customwas quenched with water (2 mL)
  3. extractionwas extracted with EtOAc (2×15 mL)
  4. extractionThe combined EtOAc extract
  5. washwas washed with water (5 mL), brine (5 mL)
  6. dry with materialwas dried over Na2SO4
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-233c2086a3114b9fa443066f53380a58
Source dataset
uspto-grants-2014_06
Patent number
US08748606B2

Reaction notes

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