Hydrochloric Acid → 7-Benzylamino-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid

HRID 1026905Notes

Reaction equation

[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:13]2[N:12]=[CH:11][C:10]=1[C:23]([O:25]C)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[Li+].Cl>N1C=CC=CC=1>[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:13]2[N:12]=[CH:11][C:10]=1[C:23]([OH:25])=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 95 °C

Procedure

Methyl 7-benzylamino-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidine-6-carboxylate (6.4 g, 17.7 mmol) obtained in step 3 was dissolved in pyridine (90 mL), lithium iodide (23.7 g, 0.18 mol) was added, and the mixture was stirred with heating at 95° C. for 4 hr. The reaction mixture was allowed to cool, added dropwise to 2 mol/L hydrochloric acid containing ice (about 500 mL), and the mixture was stirred at room temperature for 1 hr. The precipitated solid was collected by filtration, washed with isopropanol (100 mL), and dried under reduced pressure at 50° C. overnight to give the title compound (5.2 g, 85%).

Workup

temperatureto cool
stirringthe mixture was stirred at room temperature for 1 hr
filtrationThe precipitated solid was collected by filtration
washwashed with isopropanol (100 mL)
customdried under reduced pressure at 50° C. overnight

Sources & evidence

ORD record: ord-2511de564345421aa1cb6b3f581421ee
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729264B2

Reaction notes

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