Sodium methanethiolate → 2-Methylsulfanyl-4-morpholin-4-yl-6-morpholin-4-ylmethyl-thieno[3,2-d]pyrimidine

HRID 1922874Notes

Reaction equation

HRID 1922874 reaction equation
Cl[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]([CH2:11][N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.[CH3:24][S-:25].[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:24][S:25][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]([CH2:11][N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 574940512-Chloro-4-morpholin-4-yl-6-morpholin-4-ylmethyl-thieno[3,2-d]pyrimidine

Product 1

HCID 596054602-Methylsulfanyl-4-morpholin-4-yl-6-morpholin-4-ylmethyl-thieno[3,2-d]pyrimidineYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-4-morpholin-4-yl-6-morpholin-4-ylmethyl-thieno[3,2-d]pyrimidine (0.2 g, 0.56 mmol) in DMF (3 mL) was treated with sodium thiomethoxide (0.12 g, 1.71 mmol) in a sealed tube and the reaction mixture heated at 100° C. with stirring. After 2 h the contents of the tube were diluted with EtOAc, washed with saturated aqueous NaHCO3 (×2) then brine, and the organic phase was isolated, dried (Na2SO4), filtered and concentrated to afford the title compound as a light brown solid (0.205 g, 100%). LCMS (Method D): RT=1.80 min, [M+H]+ 366.

Workup

  1. washwashed with saturated aqueous NaHCO3 (×2)
  2. custombrine, and the organic phase was isolated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-07772c2fa8eb4261894e2cab344d62d2
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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