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

HRID 450116Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 7-(2-fluoro-4-iodo-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid ethyl ester (230 mg, 0.54 mmol) in a mixture of dioxane (2 mL) and water (1 mL) was added lithium hydroxide monohydrate (45 mg, 1.08 mmol). The reaction was heated at 60° C. for 1 hour. Aqueous hydrochloric acid (1M) was added dropwise until pH˜5 causing a precipitate to form. The reaction mixture was filtered and the solid residue washed with ethyl acetate (5 mL) to yield the title compound as an off white solid (67 mg, 31%). LCMS (Method B): RT=3.22 min, M+H+=398.

Workup

customto form
filtrationThe reaction mixture was filtered
washthe solid residue washed with ethyl acetate (5 mL)

Sources & evidence

ORD record: ord-8ffbcf5384124647bde7fa0b5364d5bf
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486963B2

Reaction notes

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