Methyl iodide → HCID 66801670, compound

HRID 2366234Notes

Reaction equation

HRID 2366234 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[S:10][C:11]2[C:16]([SH:17])=[N:15][CH:14]=[N:13][C:12]=2[N:18]=1.[CH2:19](N(CC)CC)C.CI>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[S:10][C:11]2[C:16]([S:17][CH3:19])=[N:15][CH:14]=[N:13][C:12]=2[N:18]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 178527887HCID 178527887, compound

Product 1

HCID 66801670HCID 66801670, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(2,6-dichlorophenyl)thiazolo[4,5-d]pyrimidine-7-thiol (1.29 g, 4.1 mmol) and triethylamine (1.66 g, 16.4 mmol) in ethanol (20 mL) was added methyl iodide (2.32 g, 16.4 mmol). The reaction mixture was stirred at room temperature for 1 hour and then concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluting with 0-20% EtOAc/hexane gradient to give the desired compound as a white solid (0.59 g, 44% yield). 1H NMR (500 MHz, CDCl3) δ 9.12 (s, 1H), 7.49-7.47 (M, 2H), 7.45-7.40 (m, 1H), 2.81 (s, 3H). LCMS (ESI) m/z: 328.9 [M+H+].

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified by silica gel column chromatography
  3. washeluting with 0-20% EtOAc/hexane gradient

Sources & evidence

ORD record
ord-7fb524c9e54f47c89b9cee7048c7f474
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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