Methyl iodide → HCID 620875, compound

HRID 1110099Notes

Reaction equation

HRID 1110099 reaction equation
Cl[S:2]([C:5]1[CH:6]=[CH:7][C:8]2[NH:14][C:13]3[N:15]=[CH:16][CH:17]=[CH:18][C:12]=3[NH:11][C:10](=[O:19])[C:9]=2[CH:20]=1)(=O)=O.[C:21]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CI>O1CCOCC1>[CH3:21][S:2][C:5]1[CH:6]=[CH:7][C:8]2[NH:14][C:13]3[N:15]=[CH:16][CH:17]=[CH:18][C:12]=3[NH:11][C:10](=[O:19])[C:9]=2[CH:20]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11776TriphenylphosphineHCID 15050927HCID 15050927, compound

Product 1

HCID 620875HCID 620875, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Intermediate 7, freshly prepared from 6 (0.5 g, 2.4 mmol) , was reduced with triphenylphosphine (2.8 g, 11.0 mmol) in dioxane (20 mL) for 2 h at 90° C. See Oae, S.; Togo, H., Bull. Chem. Soc. Jpn., 1983, 56, 3802, which is specifically incorporated by reference herein. The crude 8-thio-derivative was quenched (10 min, 25° C.) with excess methyl iodide (0.5 mL, 8.0 mmol) and crystallized from toluene to yield 50 mg (8% from 6) of 8 as a waxy solid: 1H NMR (CDCl3) δ 2.40 (s, 3 H, CH3), 6.25 (br s, 1 H, NH), 6.66 (d, J=8.3, 1 H), 6.86 (dd, J=7.7, 4.4 Hz, 1 H), 7.06 (d, J=8.2 Hz, 1 H), 7.24 (dd, J= 8.3, 2.3 Hz, 1 H), 7.79 (d, 13 J=2.3 Hz, 1 H), 7.91 (d, J=4.5 Hz, 1 H); MS (CI/NH3) m/e 258 (MH+, base), 243,211, 113.

Workup

  1. customcrystallized from toluene
  2. customto yield 50 mg (8% from 6) of 8 as a waxy solid

Sources & evidence

ORD record
ord-b3e87a34289a4a06884b4c6e54f8ade9
Source dataset
uspto-grants-1994_06
Patent number
US05324832

Reaction notes

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