Dimethylformamide → HCID 66934081, compound

HRID 1365294Notes

Reaction equation

HRID 1365294 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 was purified 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
  10. customThis crude product was purified by flash chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-e3a7d60d2d774e85a788acef0af1bdf5
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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