Hydrochloric Acid → HCID 66614346, compound

HRID 510071Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][N:5]=[C:4]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[N:14]=2)[N:3]=1.[OH-].[Na+].Cl>O1CCOCC1>[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[N:14]=2)[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1000 mg (2.55 mmol) of ethyl 4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-5-carboxylate (example 101A) were suspended in 80 ml of dioxane and admixed cautiously with 50.1 ml (948 mmol) of aqueous sodium hydroxide solution (50% by weight). The mixture was then stirred at 60° C. for 4 h and then poured onto 200 ml of ice-water. Concentrated hydrochloric acid was used to cautiously adjust the mixture to pH 2, and the precipitate observed was removed by means of filtration. The precipitate was washed with a little water and finally dried under high vacuum. Thus, 993 mg (approx. 105% of theory, the batch probably still contained small amounts of inorganic salts) of the target compound were obtained.

Workup

customthe precipitate observed was removed by means of filtration
washThe precipitate was washed with a little water
customfinally dried under high vacuum
customThus, 993 mg (approx. 105% of theory, the batch probably still contained small amounts of inorganic salts) of the target compound were obtained

Sources & evidence

ORD record: ord-1a27d821a8314bc4a846a433d9d38ef1
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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