Hydrochloric Acid → HCID 57635830, compound

HRID 2109948Notes

Reaction equation

[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][N:14]=[C:13]([S:22][CH3:23])[N:12]=2)[N:7]([C:24]2[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=2[CH3:31])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>C(O)C.C1COCC1.O>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[CH:15][N:14]=[C:13]([S:22][CH3:23])[N:12]=2)[N:7]([C:24]2[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=2[CH3:31])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of ethyl 4-{[3-tert-butyl-1-(2,5-dimethylphenyl)-1H-pyrazol-5-yl]amino}-2-(methylthio)pyrimidine-5-carboxylate (71 mg, 0.16 mmol) in a mixture of ethanol (0.5 mL) and THF (0.5 mL) was added lithium hydroxide monohydrate (68 mg, 1.6 mmol) in water (1 mL), and the mixture was then heated to 40° C. for 1 h. The reaction mixture was cooled to rt, the pH of the solution was adjusted to 5 by addition of 0.5 N hydrochloric acid, and the mixture was concentrated to dryness. The crude mixture was redissolved in methanol and subjected to HPLC purification using a gradient elution from 30% to 90% acetonitrile in water to afford 66 mg (99%) of the desired product. 1H NMR (300 MHz, CD2Cl2) δ 10.50 (s, 1H), 8.65 (s, 1H), 7.17 (dd, 2H), 7.12 (s, 1H), 6.83 (s, 1H), 2.68 (s, 3H), 2.27 (s, 3H), 1.97 (s, 3H), 1.35 (s, 9H); ES-MS m/z 412.2 (MH+); HPLC RT (min) 3.94.

Workup

temperatureThe reaction mixture was cooled to rt
concentrationthe mixture was concentrated to dryness
dissolutionThe crude mixture was redissolved in methanol
customsubjected to HPLC purification
washa gradient elution from 30% to 90% acetonitrile in water

Sources & evidence

ORD record: ord-e274d42364364b24a76d64a3c3f1ec8f
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517878B2

Reaction notes

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