Sodium Hydroxide → 4-(2,5-Dichloro-phenoxy)-pyrimidine-5-carboxylic acid

HRID 1967057Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7]([O:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[Cl:20])=[N:8][CH:9]=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+]>O1CCCC1.O>[Cl:20][C:14]1[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=1[O:12][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[CH:9][N:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 515 mg (1.64 mmol) 4-(2,5-dichloro-phenoxy)-pyrimidine-5-carboxylic acid ethyl ester in 10 mL tetrahydrofuran/water (2/1 v/v) was added 3.29 mL (3.28 mmol) 1M aqueous sodium hydroxide solution and the resulting solution was heated by microwave irradiation (Emrys Optimizer, Personal Chemistry) 30 minutes at 80° C. Solvents were evaporated under vacuum and the residue extracted three times with ethyl acetate and 1M aqueous hydrochloric acid. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to give 385 mg (57%) of the desired compound as an off-white powder. MS (ESI): m/z=238.8 [M−H]−.

Workup

customSolvents were evaporated under vacuum
extractionthe residue extracted three times with ethyl acetate and 1M aqueous hydrochloric acid
dry with materialThe combined organic layers were dried over magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-0b83a65cd6144732b73928af288d1c6b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420647B2

Reaction notes

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