Hydrochloric Acid → 7-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-ol

HRID 916669Notes

Reaction equation

[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]=[C:16](NN)[C:15]=3[CH2:22][CH2:23][CH3:24])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:25][C:26]([NH2:28])=[O:27].O.Cl>CN1C(=O)CCC1>[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]4[N:25]=[C:26]([OH:27])[N:28]=[C:16]4[C:15]=3[CH2:22][CH2:23][CH3:24])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To the solution of 131 (3.27, 10 mmol) in anhydrous NMP (3.6 mL) under nitrogen is added urea (1.60 g, 26 mmol). The resulting mixture is heated to 160° C. and stirred for 6 hours. On cooling, the reaction mixture is poured into water (80 mL), pH is adjusted to 7 with hydrochloric acid, and the solution is extracted with dichloromethane (50 ml×4). The organic solution is dried with anhydrous sodium sulfate and concentrated to give the crude product 177 as an oil which is used directly in the next step reaction.

Workup

temperatureOn cooling
extractionthe solution is extracted with dichloromethane (50 ml×4)
dry with materialThe organic solution is dried with anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-4cf7ddd6f82947faabb92497b632d52c
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271170B2

Reaction notes

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