Dichloromethane → 5-(2-Amino-4-methyl-pyrimidin-5-yl)-N-benzo[1,3]dioxol-5-yl-2-trifluoromethyl-benzenesulfonamide

HRID 2382607Notes

Reaction equation

HRID 2382607 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][S:11]([C:14]3[CH:19]=[C:18](Cl)[CH:17]=[CH:16][C:15]=3[C:21]([F:24])([F:23])[F:22])(=[O:13])=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:25][C:26]1[C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=[C:28]([NH2:41])[N:27]=1.C(Cl)Cl>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]>[NH2:41][C:28]1[N:27]=[C:26]([CH3:25])[C:31]([C:18]2[CH:17]=[CH:16][C:15]([C:21]([F:24])([F:23])[F:22])=[C:14]([S:11]([NH:10][C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)(=[O:13])=[O:12])[CH:19]=2)=[CH:30][N:29]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 529879064-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyrimidin-2-amine2×HCID 68722727N-Benzo[1,3]dioxol-5-yl-5-chloro-2-trifluoromethyl-benzenesulfonamide

Product 1

HCID 687251005-(2-Amino-4-methyl-pyrimidin-5-yl)-N-benzo[1,3]dioxol-5-yl-2-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

N-Benzo[1,3]dioxol-5-yl-5-chloro-2-trifluoromethyl-benzenesulfonamide (0.088 g, 0.23 mmol), 4-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-ylamine (Intermediate G, prepared according to WO 2007/084786, p. 92) (0.082 g, 0.34 mmol) and PdCl2(dppf).DCM (0.0185 g, 0.023 mmol) are placed in a microwave vial containing degassed DME (2 ml) and 2M Na2CO3 (0.23 ml). The resulting mixture is heated using microwave radiation at 120° C. for 60 minutes. After evaporation of the solvent, the reaction mixture is purified by flash chromatography on silica eluting with cyclohexane/EtOAc (1:2) to afford the title compound.

Workup

  1. additioncontaining
  2. customdegassed DME (2 ml) and 2M Na2CO3 (0.23 ml)
  3. temperatureThe resulting mixture is heated
  4. customat 120° C.
  5. customfor 60 minutes
  6. customAfter evaporation of the solvent
  7. customthe reaction mixture is purified by flash chromatography on silica eluting with cyclohexane/EtOAc (1:2)

Sources & evidence

ORD record
ord-3aa26c607ebe426da467fad53c3159e0
Source dataset
uspto-grants-2012_09
Patent number
US08263585B2

Reaction notes

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