Sodium methanethiolate → HCID 59605540, compound

HRID 1922873Notes

Reaction equation

HRID 1922873 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([CH2:18][CH:19]4[CH2:21][CH2:20]4)[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.[CH3:28][S-:29].[Na+]>CN(C=O)C.CCOC(C)=O>[CH:19]1([CH2:18][N:15]2[CH2:16][CH2:17][N:12]([CH2:11][C:9]3[S:10][C:5]4[C:4]([N:22]5[CH2:27][CH2:26][O:25][CH2:24][CH2:23]5)=[N:3][C:2]([S:29][CH3:28])=[N:7][C:6]=4[CH:8]=3)[CH2:13][CH2:14]2)[CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 57493980HCID 57493980, compound

Product 1

HCID 59605540HCID 59605540, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-6-(4-(cyclopropylmethyl)piperazin-1-ylmethyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidine (0.2 g, 0.49 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 hours the contents of the tube were diluted with EtOAc then washed with saturated aqueous NaHCO3 (×2) followed by brine and the organic phase was isolated, dried (Na2SO4), filtered and concentrated to afford 6-(4-(cyclopropylmethyl)piperazin-1-ylmethyl)-2-methylsulfanyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine as a pale yellow solid (0.2 g, 97%). LCMS (Method D): RT=2.04 min, [M+H]+ 419

Workup

  1. washthen washed with saturated aqueous NaHCO3 (×2)
  2. customthe organic phase was isolated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8e9ec3d05aff4fc0b997bc1afaa82f0e
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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