Benzyl Alcohol → HCID 20528989, compound

HRID 66740Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[C:4]([CH3:9])[N:3]=1.[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[NH2:1][C:2]1[C:7]([O:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][C:5]([CH3:8])=[C:4]([CH3:9])[N:3]=1

Participants

Reactant 2

HCID 244Benzyl Alcohol

HCID 2227635,6-dimethylpyrazin-2-amine

Product 1

HCID 20528989HCID 20528989, compound

Procedure

The known 2-amino-5,6-dimethylpyrazine can be brominated by Preparation 72, Step A method, and then reacted with benzyl alcohol by Preparation 45 method to provide 2-amino-3-benzyloxy-5,6-dimethylpyrazine. The 2-amino group is converted to the 2-hydroxy by the method described by Sharp et al, ibid., (see Route III) which when treated with phosphorus oxychloride by Preparation 13, Step B method, there is obtained 2-chloro-3-benzyloxy-5,6-dimethylpyrazine.

Sources & evidence

ORD record: ord-f0f4bb6d3a3f41028ebbea47dc8bf493
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04343802

Reaction notes

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