Ethanol → Ethyl 2-iodo-6-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-3-carboxylate

HRID 920818Notes

Reaction equation

[I:1][C:2]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]2[C:6](=O)[NH:7][CH:8]([CH3:10])[CH2:9][N:4]2[N:3]=1.B.C1COCC1.C(O)C>C1COCC1>[I:1][C:2]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]2[CH2:6][NH:7][CH:8]([CH3:10])[CH2:9][N:4]2[N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of Intermediate 340B (4.0 g, 11.46 mmol) in THF (40 mL) was added BH3.THF (40.1 mL, 80 mmol, 1M in THF) and the reaction mixture was stirred at 70° C. for 16 h. Ethanol (10 mL) was added and the reaction mixture was heated to reflux for 1 h. The reaction mixture was concentrated to afford Intermediate 340C (1.9 g, 40% yield) as a pale brown liquid. MS(ES): m/z=336 [M+H]+. The crude compound was taken to the next step without further purification.

Workup

temperaturethe reaction mixture was heated
temperatureto reflux for 1 h
concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-3a649b86491b4a6bb77aa35ffc89fbf8
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273058B2

Reaction notes

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