Benzyl Bromide → HCID 66759164, compound

HRID 718228Notes

Reaction equation

HRID 718228 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.C(N(CC)CC)C.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CS(C)=O>[CH2:26]([S:18][C:4]1[C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[S:8][C:6]=2[N:7]=[C:2]([NH2:1])[N:3]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 178509029HCID 178509029, compound

Product 1

HCID 66759164HCID 66759164, 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 (50 mg, 0.18 mmol) and triethylamine (63 μl, 0.45 mmol) in DMSO (1 ml) was added benzyl bromide (43 μl, 0.36 mmol). The reaction mixture was stirred under N2 at 25° C. for 3 hours. The mixture was poured onto water and extracted with EtOAc. The organic extracts were dried over Na2SO4 and the solvents were removed under reduced pressure. The residue was purified by flash chromatography on silica (CH2Cl2/MeOH 100:1) to yield the title compound as a light yellow solid (40 mg, 60%).

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. customthe solvents were removed under reduced pressure
  5. customThe residue was purified by flash chromatography on silica (CH2Cl2/MeOH 100:1)

Sources & evidence

ORD record
ord-e9a09f2706aa4877896bd8b41cc11ac7
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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