Hydrochloric Acid → 7-(2-Fluoro-4-methylsulfanyl-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid

HRID 450120Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:12]=[CH:11][N:10]=[CH:9][N:8]2[C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][C:16]=1[F:23])=[O:4].O.[OH-].[Li+].Cl>O1CCOCC1.O>[F:23][C:16]1[CH:17]=[C:18]([S:21][CH3:22])[CH:19]=[CH:20][C:15]=1[NH:14][C:13]1[N:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:7]2=[CH:6][C:5]=1[C:3]([OH:4])=[O:2]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 7-(2-fluoro-4-methylsulfanyl-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid methyl ester (635 mg, 1.9 mmol) in dioxane (8 mL) and water (2.5 mL) was added lithium hydroxide monohydrate (161 mg, 3.8 mmol). The reaction was stirred at 55° C. for 2 hours then cooled to room temperature. Aqueous hydrochloric acid (1M) was added dropwise until pH˜3. The reaction mixture was extracted twice with ethyl acetate (2×10 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a dark brown solid (600 mg, 99%). LCMS (Method B): RT=3.20 min, M+H+=318.

Workup

temperaturethen cooled to room temperature
extractionThe reaction mixture was extracted twice with ethyl acetate (2×10 mL)
washThe combined organic fractions were washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0a36e9c66b1e4e5b9fac87b4ae74179a
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486963B2

Reaction notes

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