Methyl iodide → HCID 20221547, compound

HRID 980468Notes

Reaction equation

HRID 980468 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[N:7][CH:6]=[C:5]([CH3:9])[N:4]=1.[CH3:10][I:11]>CCOCC>[I-:11].[CH3:10][N+:7]1[CH:6]=[C:5]([CH3:9])[N:4]=[C:3]([CH2:2][OH:1])[CH:8]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 580062(6-Methylpyrazin-2-yl)methanol

Product 1

HCID 20221547HCID 20221547, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.0 g of 2-hydroxymethyl-6-methylpyrazine (401), prepared by the known method of Klein, et al., J. Org. Chem., 26, 126(1961), was dissolved in 5 ml of ether and 5 ml of methyl iodide added. The flask was stoppered and stored in the dark for 2 weeks. The ether was decanted and the resultant semi-solid material recrystallized from ethanol/ethyl acetate giving 1.8 g of a yellow solid, product (400) m.p. 153°-4°. UV H2O max: 226 (4.13), 287 (3.89). 13C NMR: 163.33, S, 161.73, S (C3, C5); 136.85, D, 133.10, D (C2,C6); 62.79, T (CH2OH); 49.74, Q (NCH3); 22.19, Q (ArCH3). 1HNMR: 8.80, S, 8.76, S (H2, H6): 4.97, S (CH2OH); 4.44, S (NCH3); 2.79, S (ArCH3).

Workup

  1. waitstored in the dark for 2 weeks
  2. customThe ether was decanted
  3. customthe resultant semi-solid material recrystallized from ethanol/ethyl acetate giving 1.8 g of a yellow solid, product (400) m.p. 153°-4°

Sources & evidence

ORD record
ord-c0fb13144b8446a49ea33f21f46190cf
Source dataset
uspto-grants-1987_01
Patent number
US04638005

Reaction notes

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