Dimethylformamide → HCID 66934081, compound

HRID 390975Notes

Reaction equation

HRID 390975 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]3)=[C:8]([CH3:22])[C:6]=2[N:7]=1.[CH3:29][S-:30].[Na+].CN(C=O)C>C1(C)C=CC=CC=1>[CH3:22][C:8]1[C:6]2[N:7]=[C:2]([S:30][CH3:29])[N:3]=[C:4]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:5]=2[S:10][C:9]=1[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 86623537HCID 86623537, compound

Product 1

HCID 66934081HCID 66934081, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Chloro-7-methyl-4-morpholino-6-((4-N-methylsulfonylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidine (2.38 mM) was added to sodium thiomethoxide dissolved in 50 mL toluene under N2 and heated to reflux. The reaction was stirred at reflux 24 hours and there was very little product by LCMS. To this reaction mixture was added 50 mL DMF to dissolve the starting material and again heated to reflux for two hours. Complete product formation was confirmed by LCMS. The reaction was poured onto ice water, extracted with ether, dried over MgSO4, and concentrated in vacuo. This crude product waspurified by flash chromatography (MeOH/DCM) giving 7-methyl-2-(methylthio)-4-morpholino-6-((4-N-methylsulfonylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidine. MS (Q1) 445 (M+)

Workup

  1. temperatureheated to reflux
  2. temperatureat reflux 24 hours
  3. dissolutionto dissolve the starting material
  4. temperatureagain heated
  5. temperatureto reflux for two hours
  6. additionThe reaction was poured onto ice water
  7. extractionextracted with ether
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8caa1f5a015c41eaaebe98f72bb9c3ee
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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