Potassium Carbonate → (3-(1-isopropyl-1H-pyrazol-5-yl)pyrazin-2-yl)methanol

HRID 1471719Notes

Reaction equation

Cl[C:2]1[C:3]([CH2:8][OH:9])=[N:4][CH:5]=[CH:6][N:7]=1.[CH:10]([N:13]1[C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][CH:15]=[N:14]1)([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH:10]([N:13]1[C:17]([C:2]2[C:3]([CH2:8][OH:9])=[N:4][CH:5]=[CH:6][N:7]=2)=[CH:16][CH:15]=[N:14]1)([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of (3-chloropyrazin-2-yl)methanol (200 mg, 1.4 mmol, 1 eq.), 1-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (393 mg, 1.67 mmol, 1.2 eq.), Pd(dppf)Cl2 (102 mg, 0.14 mmol, 0.1 eq.), and K2CO3 (580 mg, 4.2 mmol, 3 eq.) in a RB flask were added dioxane (6 mL) and water (2 mL). The mixture was heated at 100° C. for 1 h, cooled to rt, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-(1-isopropyl-1H-pyrazol-5-yl)pyrazin-2-yl)methanol (110 mg, 36%) as a yellow oil. LRMS (M+H+) m/z 219.1.

Workup

temperaturecooled to rt
filtrationfiltered
concentrationconcentrated
custompurified on silica gel using
additiona mixture of EtOAc and hexanes as eluent

Sources & evidence

ORD record: ord-5101fc679f294a8e8f759a855a31af51
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012450B2

Reaction notes

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