Dichloromethane → Pyrazolo[1,5-a]pyrimidin-7-amine

HRID 2047172Notes

Reaction equation

C1(C2C=CC(B3OC(C)(C)C(C)(C)O3)=CN=2)C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl.Cl[C:34]1[CH:39]=[C:38]([N:40](COCC[Si](C)(C)C)COCC[Si](C)(C)C)[N:37]2[N:57]=[CH:58][C:59](I)=[C:36]2[N:35]=1>O1CCOCC1.O.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]>[N:57]1[N:37]2[C:38]([NH2:40])=[CH:39][CH:34]=[N:35][C:36]2=[CH:59][CH:58]=1

Participants

Conditions

Temperature: 70 °C

Procedure

2-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.38 mmol, 675 mg), K3PO4 (5.96 mmol, 1264 mg), and PdCl2(dppf).CH2Cl2 (0.20 mmol, 162 mg) were added to a solution of 5-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (1.98 mmol, 1101 mg) in dioxane (18 mL) and H2O (3 mL). The resulting solution was stirred at 70° C. under argon overnight. The mixture was diluted with H2O and then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation and purification by column chromatography afforded 5-chloro-3-(6-phenylpyridin-3-yl)-N,N-bis((2 trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine: LCMS tR=3.36 Min (5 min run, UV254nm). Mass calculated for, M+ 581.2, observed LC/MS m/z 582.2 (M+H).

Workup

extractionextracted with ethyl acetate (×2)
washThe combined organic layers were washed with brine
dry with materialdried with Na2SO4
customEvaporation and purification by column chromatography

Sources & evidence

ORD record: ord-e33f31ec1c46431cbafbb58d2c437c3c
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08591943B2

Reaction notes

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