Triethylamine → Carbamic acid, N-[1-[6-chloro-2-(methylthio)-4-pyrimidinyl]-4-piperidinyl]-, 1,1-dimethylethyl ester

HRID 1529455Notes

Reaction equation

HRID 1529455 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[CH3:11][C:12]([O:15][C:16]([NH:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:17])([CH3:14])[CH3:13].CCN(CC)CC>C(Cl)Cl>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([N:22]2[CH2:21][CH2:20][CH:19]([NH:18][C:16](=[O:17])[O:15][C:12]([CH3:13])([CH3:11])[CH3:14])[CH2:24][CH2:23]2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 60137165Carbamic acid, N-[1-[6-chloro-2-(methylthio)-4-pyrimidinyl]-4-piperidinyl]-, 1,1-dimethylethyl esterYield 103.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 100-mL round-bottomed flask was added 4,6-dichloro-2-(methylthio)pyrimidine (2.0 g, 10.25 mmol, Sigma-Aldrich) and 4-(n-boc-amino)-piperidine (2.053 g, 10.25 mmol, Sigma-Aldrich) in DCM (25 mL) followed by Et3N (2.139 mL, 15.38 mmol). The reaction was stirred at RT for 5 h, then diluted with DCM (100 mL). The mixture was washed with water, brine, dried MgSO4, filtered and concentrated to give crude tert-butyl 1-(6-chloro-2-(methylthio)pyrimidin-4-yl)piperidin-4-ylcarbamate (3.80 g, 100%) as a white solid. MS (ESI, pos. ion) m/z: 359.0 (M+1).

Workup

  1. washThe mixture was washed with water, brine, dried MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-aff8d40c24f04975a24192914b82e463
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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