Methanol → 2-(4-(Azetidin-3-yl)piperazin-1-yl)pyrimidine

HRID 2408271Notes

Reaction equation

HRID 2408271 reaction equation
C([N:14]1[CH2:17][CH:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[N:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[CH2:20][CH2:19]2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.ClC(OC(Cl)C)=O.CO.C(OCC)C>C(Cl)Cl>[NH:14]1[CH2:17][CH:16]([N:18]2[CH2:19][CH2:20][N:21]([C:24]3[N:25]=[CH:26][CH:27]=[CH:28][N:29]=3)[CH2:22][CH2:23]2)[CH2:15]1

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 5213051-Chloroethyl chloroformateHCID 66770498HCID 66770498, compound

Product 1

HCID 534408612-(4-(Azetidin-3-yl)piperazin-1-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[4-(1-benzhydryl-azetidin-3-yl)-piperazin-1-yl]-pyrimidine (2.03 g, 5.27 mmol) in CH2Cl2 (20 mL) was added 1-chloroethyl chloroformate (1.704 mL, 15.79 mmol) at 0° C. under N2. The resulting mixture was stirred at 0° C. for 90 min and then methanol (4 mL) was added. The resulting mixture was refluxed for 1 h, then cooled. Diethyl ether (40 mL) was added to the resulting mixture. The solid was filtered and dried to yield 2-(4-azetidin-3-yl-piperazin-1-yl)-pyrimidine, which was used in the next step without further purification.

Workup

  1. temperatureThe resulting mixture was refluxed for 1 h
  2. temperaturecooled
  3. filtrationThe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-f61cf28dc69545f1a5a91b2adfb3bf51
Source dataset
uspto-grants-2014_08
Patent number
US08815839B2

Reaction notes

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