Triphenylarsine → 4-Chloro-6-(1-methylpyrazol-4-yl)thieno[3,2-d]pyrimidine

HRID 1818951Notes

Reaction equation

HRID 1818951 reaction equation
Br[C:2]1[S:10][C:9]2[C:8]([Cl:11])=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[CH3:12][N:13]1[CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:15]=[N:14]1.[As](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.OP([O-])([O-])=O.[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.CN(C=O)C>[Cl:11][C:8]1[C:9]2[S:10][C:2]([C:16]3[CH:15]=[N:14][N:13]([CH3:12])[CH:17]=3)=[CH:3][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

8

Reactant 4

HCID 11773TriphenylarsineHCID 24450Potassium Phosphate, DibasicHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 183827966-Bromo-4-chlorothieno(3,2-d)pyrimidine

Product 1

HCID 860949964-Chloro-6-(1-methylpyrazol-4-yl)thieno[3,2-d]pyrimidine

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-bromo-4-chloro-thieno[3,2-d]pyrimidine (4.0 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (4.4 mmol), Pd2(dba)3 (0.8 mmol), Ph3As (0.8 mmol) and K2HPO4(8.0 mmol) in a DMF (40 mL) and water (10 mL) are stirred at room temperature until the reaction was complete. The reaction is partitioned between EtOAc and water, washed with brine, dried, concentrated and purified by flash column chromatography on silica gel to give 4-chloro-6-(1-methyl-1H-pyrazol-4-yl)-thieno[3,2-d]pyrimidine (compound 58.4).

Workup

  1. customThe reaction is partitioned between EtOAc and water
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-b419dc85024545f5bbcbbfd4ff00f313
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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