Hydrochloric Acid → 5-Amino-3-(cyclopropylmethoxy)pyrazine-2-carbonitrile

HRID 40660

Reaction equation

[H-].[Na+].[CH:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.[NH2:8][C:9]1[N:10]=[C:11](Cl)[C:12]([C:15]#[N:16])=[N:13][CH:14]=1.Cl>O1CCOCC1>[NH2:8][C:9]1[N:10]=[C:11]([O:7][CH2:6][CH:3]2[CH2:5][CH2:4]2)[C:12]([C:15]#[N:16])=[N:13][CH:14]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of sodium hydride (93 mg, 3.882 mmol) in dioxane (4 mL) was added cyclopropylmethanol (280 mg, 3.882 mmol) dropwise. The solution was stirred for 30 minutes and then 5-amino-3-chloropyrazine-2-carbonitrile (300 mg, 1.941 mmol) was added and the reaction mixture heated at 90° C. for 14 hours. The reaction mixture was poured into aqueous HCl (1 M) and extracted with ethyl acetate. The aqueous layer was re-extracted with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to dryness to give the title compound (305 mg, 1.605 mmol, 83%) which was used in subsequent steps without further purification. LC-MS (3) Rt=1.49 min; m/z (ESI+) 191 (M+H+).

Workup

extractionextracted with ethyl acetate
extractionThe aqueous layer was re-extracted with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-99953e524ebb411787feb18a6c23ffa0
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530468B2

Linked notes

Loading…