Dimethyl Sulfate → HCID 86753496, compound

HRID 1459733Notes

Reaction equation

HRID 1459733 reaction equation
[CH3:1][O:2][S:3]([O:6]C)(=[O:5])=[O:4].[CH3:8][N:9]([CH2:11][C:12]1[C:20]2[C:15](=[CH:16][N:17]=[C:18]([N:21]3[CH:25]=[N:24][CH:23]=[N:22]3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:10]>C1COCC1>[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].[N:21]1([C:18]2[CH:19]=[C:20]3[C:12]([CH2:11][N+:9]([CH3:1])([CH3:8])[CH3:10])=[CH:13][NH:14][C:15]3=[CH:16][N:17]=2)[CH:25]=[N:24][CH:23]=[N:22]1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 67651615HCID 67651615, compound

Product 1

HCID 86753496HCID 86753496, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of dimethylsulphate (0.13ml, 1.4 mmol) and dry THF (5ml) was cooled to 0° C. under nitrogen and N,N-dimethyl-[5-(1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]methylamine (0.15 g, 0.62 mmol) was added portionwise over a period of 5 min. The mixture was stirred at 0° C. for 90 min. The resulting precipitate was collected by filtration and washed with THF to afford the title compound (0.23 g, 100%) as a colourless solid; mp 182°-185° C. 1H NMR (250 MHz, d6 -DMSO) δ 3.06 (9H, s), 3.38 (3H, s), 4.77 (2H, s), 8.08 (1H, s), 8.30 (1H, s), 8.38 (1H, s), 8.78 (1H, s), 9.31 (1H, s), 12.40 (1H, br s).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with THF

Sources & evidence

ORD record
ord-dce47917bbfa442285ae15368887feae
Source dataset
uspto-grants-1998_12
Patent number
US05854268

Reaction notes

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