Sodium methanethiolate → HCID 68717795, compound

HRID 888953Notes

Reaction equation

HRID 888953 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][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)=[N:18][C:17]=3[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:31][S-:32].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][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]([S:32][CH3:31])=[N:18][C:17]=3[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolate2×HCID 57494058Tert-butyl 4-((2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazine-1-carboxylate

Product 1

HCID 68717795HCID 68717795, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester (100 mg, 0.22 mmol) and sodium thiomethoxide (30 mg, 0.44 mmol) in DMF was heated at 100° C. in a sealed tube under nitrogen for 1 h. More sodium thiomethoxide (15 mg, 0.22 mmol) was added, and the heating pursued for 1 h. The mixture was left to cool to RT and was then partitioned between a sat. sodium carbonate solution and EtOAc. The organic layer was isolated, dried (MgSO4) and evaporated to dryness to afford 4-(2-methylsulfanyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester as a yellow solid (100 mg, 98%).

Workup

  1. waitThe mixture was left
  2. customwas then partitioned between a sat. sodium carbonate solution and EtOAc
  3. customThe organic layer was isolated
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-fc312e36034e4d47982534bf69b16db6
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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