Hydrochloric Acid → 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylic acid

HRID 2364683Notes

Reaction equation

[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:28]([O:30]C)=[O:29])=[C:21]5[C:25]=4[O:24][C:23]([CH3:27])([CH3:26])[CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:32])[C:8](=[O:33])[C@H:7]2[CH2:34][CH3:35])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+].O.Cl>CO>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:28]([OH:30])=[O:29])=[C:21]5[C:25]=4[O:24][C:23]([CH3:27])([CH3:26])[CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:32])[C:8](=[O:33])[C@H:7]2[CH2:34][CH3:35])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylate 4e (1.67 g, 3.48 mmol) was dissolved in 50 mL of methanol followed by the addition of 1 M lithium hydroxide solution (17.4 mL, 17.40 mmol). The reaction solution was heated to 50° C. and stirred for 12 hours. The resulting solution was added with 10 mL of water, and added dropwise with 1 M hydrochloric acid to adjust pH to 2 to 3. The reaction solution was concentrated under reduced pressure to obtain the title compound 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylic acid 4f (1.89 g, yield: 100%) as a white solid.

Workup

concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-7b83fcfa8f03494ba52154edeb4fce45
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691822B2

Reaction notes

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