Sodium Carbonate → 2-Methyl-1-(4-(2-(methylthio)pyrido[2,3-d]pyrimidin-7-yl)-1H-pyrazol-1-yl)propan-2-ol

HRID 523081Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[CH:10]=[N:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[N:13]=1.[CH3:14][C:15]([OH:32])([CH3:31])[CH2:16][N:17]1[CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=[N:18]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O>[CH3:14][C:15]([OH:32])([CH3:31])[CH2:16][N:17]1[CH:21]=[C:20]([C:2]2[CH:3]=[CH:4][C:5]3[CH:10]=[N:9][C:8]([S:11][CH3:12])=[N:7][C:6]=3[N:13]=2)[CH:19]=[N:18]1

Participants

Conditions

Temperature: 140 °C

Procedure

A suspension of 7-chloro-2-(methylthio)pyrido[2,3-d]pyrimidine (Preparation 57, 50.6 mg, 0.239 mmol), 2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol (Preparation 124, 63.6 mg, 0.239 mmol), Pd(dppf)C2•DCM (20.2 mg, 0.024 mmol), Na2CO3 (2M, 0.24 mL, 0.48 mmol) in DME (4 mL) was stirred at 140° C. under microwave irradiation for 60 minutes. The reaction mixture was diluted with EtOAc and dried with Na2SO4, filtered and concentrated in vacuo. The residue was purified using Biotage silica gel column chromatography eluting with 25-80% EtOAc/cyclohexane to give the title compound as orange semi-solid (21 mg, 28%).

Workup

dry with materialdried with Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified
washeluting with 25-80% EtOAc/cyclohexane

Sources & evidence

ORD record: ord-1af1c535bc8a4838a44064eb8887228c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334286B2

Reaction notes

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