Formic Acid → 2-Chloro-6-(1-methyl-piperidin-4-ylidenemethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

HRID 2098680Notes

Reaction equation

HRID 2098680 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]2[S:10][C:9]([CH:11]=[C:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.[CH:24](O)=O.C=O>O.ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]2[S:10][C:9]([CH:11]=[C:12]3[CH2:13][CH2:14][N:15]([CH3:24])[CH2:16][CH2:17]3)=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 866183982-Chloro-4-morpholin-4-yl-6-piperidin-4-ylidenemethyl-thieno[3,2-d]pyrimidine

Product 1

HCID 866183992-Chloro-6-(1-methyl-piperidin-4-ylidenemethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 2-chloro-4-morpholin-4-yl-6-piperidin-4-ylidenemethyl-thieno[3,2-d]pyrimidine (500 mg) and formic acid (2.5 mL) at room temperature was added formaldehyde (0.5 mL of a 37 wt % solution in water). The reaction mixture was stirred at 60° C. for 16 h. The mixture was then diluted with dichloromethane (2 mL) and washed with 2 M aqueous sodium hydroxide solution (20 mL) and brine (20 mL), dried (MgSO4), reduced in vacuo and purified by column chromatography to give 2-chloro-6-(1-methyl-piperidin-4-ylidenemethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine as a yellow solid (0.15 g).

Workup

  1. washwashed with 2 M aqueous sodium hydroxide solution (20 mL) and brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-d985268c082c41cf99d7e9430d9d1768
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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