Water → HCID 50941766, compound

HRID 718225Notes

Reaction equation

HRID 718225 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([SH:18])[C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[S:8][C:6]=2[N:7]=1.[CH2:19](N(CC)CC)C.IC.O>CS(C)=O>[F:17][C:14]1[CH:13]=[CH:12][C:11]([C:9]2[S:8][C:6]3[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([S:18][CH3:19])[C:5]=3[N:10]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 8471TriethylamineHCID 178509029HCID 178509029, compound

Product 1

HCID 50941766HCID 50941766, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-amino-2-(4-fluorophenyl)thiazolo[5,4-d]pyrimidine-7-thiol (1.2 g, 4.31 mmol) and triethylamine (1.50 ml, 10.8 mmol) in DMSO (25 ml) was added iodomethane (0.54 ml, 8.62 mmol). The reaction mixture was stirred for 12 h under N2 at 25° C. The mixture was poured into water and extracted with EtOAc. The organic extracts were dried over Na2SO4 and the solvents were removed under reduced pressure. The crude residue was purified by flash chromatography on silica (CH2Cl2/MeOH 80:1), yielding the title compound as a light yellow solid (0.76 g, 60%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic extracts were dried over Na2SO4
  3. customthe solvents were removed under reduced pressure
  4. customThe crude residue was purified by flash chromatography on silica (CH2Cl2/MeOH 80:1)

Sources & evidence

ORD record
ord-8ff93e5189394c0f93fa99513fee45e1
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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