Sodium methanethiolate → HCID 178481673, compound

HRID 32556Notes

Reaction equation

HRID 32556 reaction equation
Br[C:2]1[N:3]([CH3:23])[C:4]([C:13]2[S:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH2:22])[C:20]=3[N:21]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.C[S-:25].[Na+]>CN(C=O)C>[NH2:22][C:19]1[C:20]2[N:21]=[C:13]([C:4]3[N:3]([CH3:23])[C:2]([SH:25])=[N:6][C:5]=3[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:14][C:15]=2[N:16]=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 100687782-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine

Product 1

HCID 178481673HCID 178481673, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine (Example 26) (80 mg) and sodium thiomethoxide (58 mg) in DMF (5 mL) were heated at 80° C. for 2 hours under an inert atmosphere. After cooling to ambient temperature the reaction mixture was concentrated in vacuo, then dissolved in 2M NaOH (5 mL) and washed with DCM (5 mL). The aqueous layer was acidified to pH 4 with 2M HCl, the solid precipitate washed with water (5 mL) then diethyl ether (10 mL) and dried under high vacuum to give the title compound as a yellow solid (44 mg, 65%);

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutiondissolved in 2M NaOH (5 mL)
  3. washwashed with DCM (5 mL)
  4. washthe solid precipitate washed with water (5 mL)
  5. dry with materialdiethyl ether (10 mL) and dried under high vacuum

Sources & evidence

ORD record
ord-6cf6f5f51f804eab908673cf4006f40d
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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