Sodium methanethiolate → HCID 67261027, compound

HRID 1845876Notes

Reaction equation

HRID 1845876 reaction equation
F[C:2]1[N:7]=[C:6]([O:8][C@@H:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)[CH3:10])[CH:5]=[CH:4][CH:3]=1.[CH3:18][S-:19].[Na+]>CS(C)=O>[CH3:18][S:19][C:5]1[C:6]([O:8][CH:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)[CH3:10])=[N:7][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 67255142HCID 67255142, compound

Product 1

HCID 67261027HCID 67261027, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of (R)-4-(1-(6-fluoro-pyridin-2-yloxy)ethyl)pyrimidin-2-amine (389 mg) (prepared as described for (R)-4-(1-(6-fluoro-pyridin-2-yloxy)ethyl)pyrimidin-2-amine but starting from 1-(2-aminopyrimidin-4-yl)ethanol) in dry dimethylsulfoxide (10 mL) was added sodium methanethiolate (582 mg) the solution was stirred for 5 min and then heated with microwave irradiation at 140° C. for 300 sec. The resulting mixture was quenched into water (300 mL) the resulting solid was filtered and washed with water and dried. The solid was triturated with heptane and further to give the title compound (226 mg) as a pale brown solid, MS (ES): m/z 263 [M+H]+.

Workup

  1. customThe resulting mixture was quenched into water (300 mL) the resulting solid
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried
  5. customThe solid was triturated with heptane

Sources & evidence

ORD record
ord-4c3e1f4d96af406bab768c879cb6d666
Source dataset
uspto-grants-2015_02
Patent number
US08952001B2

Reaction notes

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