Hydrochloric Acid → 2-Chloro-4-morpholin-4-yl-6-piperidin-4-ylidenemethyl-thieno[3,2-d]pyrimidine

HRID 2098679Notes

Reaction equation

HRID 2098679 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]2[S:23][C:22]3[C:21]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[N:20][C:19]([Cl:30])=[N:18][C:17]=3[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>ClCCl.C(OCC)C>[Cl:30][C:19]1[N:20]=[C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:22]2[S:23][C:15]([CH:14]=[C:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:16][C:17]=2[N:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 866183974-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethylene)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866183982-Chloro-4-morpholin-4-yl-6-piperidin-4-ylidenemethyl-thieno[3,2-d]pyrimidineYield 80.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethylene)-piperidine-1-carboxylic acid tert-butyl ester (0.85 g) in dichloromethane (10 mL) at room temperature was added hydrogen chloride (2 mL of a 2.0 M solution in diethyl ether). The reaction mixture was stirred at room temperature for 16 h and then reduced in vacuo. The residue was redissolved in dichloromethane (10 mL) and washed with saturated sodium carbonated solution (2×10 mL) and brine (10 mL), dried (MgSO4) and reduced in vacuo to give 2-chloro-4-morpholin-4-yl-6-piperidin-4-ylidenemethyl-thieno[3,2-d]pyrimidine (0.53 g).

Workup

  1. washwashed with saturated sodium carbonated solution (2×10 mL) and brine (10 mL)
  2. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-b156b0c953af4caba610429b3ed112ca
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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