Hydrochloric Acid → 3,5-Diamino-6-chloro-pyrazine acid

HRID 69885Notes

Reaction equation

[NH2:1][C:2]1[C:3](NC(OC)=O)=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.[Li+].[OH-:16].Cl.C1[CH2:22][O:21]CC1.CO>>[NH2:1][C:2]1[C:3]([C:22]([OH:21])=[O:16])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 3939Lithium Hydroxide

HCID 21899815MeOH tetrahydrofuran

HCID 86669184HCID 86669184, compound

Product 1

HCID 64521193,5-Diamino-6-chloro-pyrazine acidYield 93%

Procedure

To a solution of methyl 3,5-diamino-6-chloropyrazine-2-carbamate (5 g, 0.025 mols) in 2:1 THF/MeOH (90 mL) was added 1M LiOH (62 mL, 0.062 mols). After the reaction was stirred at r.t. 72 hrs, 1N HCl (62 mL, 0.062 mols) was added. The reaction was filtered and washed with water (3×10 mL) to give 3,5-diamino-6-chloropyrazine-2-carboxylic acid as white solid 4.3 g (93% yield). LCMS (m/z): 189.1 (MH+); LC Rt=1.05 min.

Workup

filtrationThe reaction was filtered
washwashed with water (3×10 mL)

Sources & evidence

ORD record: ord-671c1c7fb69541e4af32669088ce1d08
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822497B2

Reaction notes

Loading…