Ammonium Chloride → 2-Amino-5,6-dichloro-3-[hydroxy(thiazol-2-yl)methyl]pyrazine

HRID 1981162Notes

Reaction equation

[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[N:6][C:5]([Cl:10])=[C:4]([Cl:11])[N:3]=1.[S:12]1[CH:16]=[CH:15][N:14]=[C:13]1[Li].[Cl-].[NH4+]>CCOCC>[NH2:1][C:2]1[C:7]([CH:8]([OH:9])[C:13]2[S:12][CH:16]=[CH:15][N:14]=2)=[N:6][C:5]([Cl:10])=[C:4]([Cl:11])[N:3]=1

Participants

Conditions

Temperature: -15 °C

Procedure

In 5 ml of ether there was dissolved 2-amino-5,6-dichloro-3-formylpyrazine (144 mg; 0.75 mMol) prepared as in Example 1, Step B above. The (thiazol-2-yl)lithium (1 mMol) prepared in Step A above was cooled to -78° C., after which the solution of 2-amino-5,6-dichloro-3-formylpyrazine was added dropwise under nitrogen. The reaction mixture was then allowed to warm up gradually to -15° C. and kept at that temperature for 30 minutes. When thin layer chromatography indicated substantial amounts of starting material remaining, additional (thiazol-2-yl)lithium was added. Ammonium chloride solution was then added and the reaction mixture was stirred for 15 minutes at -15° C. The mixture was extracted with ether, passed through a silica gel column, and eluted with dichloromethane to give the product (44 mg).

Workup

extractionThe mixture was extracted with ether
washeluted with dichloromethane

Sources & evidence

ORD record: ord-a2c5dfdb6bd440cbabc782d0fe7ec393
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04512991

Reaction notes

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