Potassium Carbonate → HCID 75204432, compound

HRID 1755252Notes

Reaction equation

HRID 1755252 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]([NH:10][C@H:11]2[CH2:15][CH2:14][N:13]([C:16]3[C:17]4[N:18]([CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:20][N:21]=3)[CH2:12]2)=[O:9])=[N:6][CH:7]=1.[CH3:25][C:26]1(C)C(C)(C)OB(C=C)O1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.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]>[C:16]1([N:13]2[CH2:14][CH2:15][C@H:11]([NH:10][C:8]([C:5]3[N:4]=[CH:3][C:2]([CH:25]=[CH2:26])=[CH:7][N:6]=3)=[O:9])[CH2:12]2)[C:17]2[N:18]([CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:20][N:21]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 75204202HCID 75204202, compound

Product 1

HCID 75204432HCID 75204432, compoundYield 46.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (S)-5-bromo-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)pyrimidine-2-carboxamide (0.10 g, 0.26 mmol, 1 eq) in 1 mL of DMF was added 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.13 g, 0.84 mmol, 3.2 eq), followed by K2CO3 (0.18 g, 1.3 mmol, 5 eq) in 0.2 mL of H2O and Pd(dppf)Cl2 (0.02 g, 0.02 mmol, 0.1 eq). After heating for 1 h at 120° C. the mixture was concentrated and purified by silica gel column chromatography (EtoAc:MeOH 1:1) followed by HPLC to afford (S)—N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)-5-vinylpyrimidine-2-carboxamide (0.040 g, 0.12 mmol, 46%).

Workup

  1. concentrationwas concentrated
  2. custompurified by silica gel column chromatography (EtoAc:MeOH 1:1)

Sources & evidence

ORD record
ord-0e007cc160a2402ca6b7fc707c09da32
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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