Methanesulfonic Acid → N2-(5-Bromo-2-isopropoxy-4-methyl-phenyl)-5-methyl-N4-[2-(propane-2-sulfonyl)-phenyl]pyrimidine-2,4-diamine

HRID 386775Notes

Reaction equation

HRID 386775 reaction equation
[Br:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[C:6]([NH2:8])[CH:7]=1.Cl[C:15]1[N:20]=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([CH:31]([CH3:33])[CH3:32])(=[O:30])=[O:29])[C:18]([CH3:34])=[CH:17][N:16]=1.CS(O)(=O)=O>CC(O)C>[Br:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([O:9][CH:10]([CH3:11])[CH3:12])=[C:6]([NH:8][C:15]2[N:20]=[C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[S:28]([CH:31]([CH3:32])[CH3:33])(=[O:30])=[O:29])[C:18]([CH3:34])=[CH:17][N:16]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 597644732-chloro-N-(2-(isopropylsulfonyl)phenyl)-5-methylpyrimidin-4-amine2×HCID 597644885-Bromo-2-isopropoxy-4-methyl-phenylamine

Product 1

HCID 59764523N2-(5-Bromo-2-isopropoxy-4-methyl-phenyl)-5-methyl-N4-[2-(propane-2-sulfonyl)-phenyl]pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5-Bromo-2-isopropoxy-4-methyl-phenylamine from the previous step (537 mg, 2.20 mmol) and 2-chloro-N-(2-(iso-propylsulfonyl)phenyl)-5-methylpyrimidin-4-amine (Intermediate 1, 652 mg, 2.00 mmol) in the presence of methanesulfonic acid (0.143 mL) in 4 mL 2-propanol are condensed at 140° C. for 30 min in a sealed tube under microwave irradiation. Following workup, N2-(5-Bromo-2-isopropoxy-4-methyl-phenyl)-5-methyl-N4-[2-(propane-2-sulfonyl)-phenyl]-pyrimidine-2,4-diamine is obtained. MS (ES+): 535.1 (MH+).

Workup

  1. customcondensed at 140° C. for 30 min in a sealed tube
  2. customunder microwave irradiation

Sources & evidence

ORD record
ord-8fcdf5ebff20472597d285f8de1df21c
Source dataset
uspto-grants-2013_02
Patent number
US08372858B2

Reaction notes

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