5-Chloropyrazinoic acid → 5-(Oxetan-2-ylmethoxy)pyrazine-2-carboxylic acid

HRID 571744Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

In a microwave vial 5-chloropyrazine-2-carboxylic acid (100.0 mg, 0.631 mmol), dimethylformamide (5 mL), oxetan-2-ylmethanol (83.4 mg, 0.946 mmol) and potassium tert-butoxide (176.9 mg, 1.58 mmol) are added. A small exotherm is observed. After 1 minute at room temperature the vial is sealed and the mixture heated at 120° C. for 30 minutes in the microwave. The reaction mixture is then quenched with aqueous NH4Cl and the solvent evaporated under reduced pressure. The resultant residue is triturated in 2-propanol. The filtrate is concentrated under reduced pressure to give the title compound as a cream solid (0.294 g, 99%) and is used without further purification. ES/MS (m/e): 211.0 (M+1), 208.8 (M−H).

Workup

customAfter 1 minute at room temperature the vial is sealed
customThe reaction mixture is then quenched with aqueous NH4Cl
customthe solvent evaporated under reduced pressure
customThe resultant residue is triturated in 2-propanol
concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record: ord-5e8954cb5c7647bbb4d1d8c8501e4832
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029367B2

Reaction notes

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