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

HRID 386786Notes

Reaction equation

HRID 386786 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([C:12]#[C:13][Si](C)(C)C)=[CH:7][C:6]=1[NH:18][C:19]1[N:24]=[C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[S:32]([CH:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])[C:22]([CH3:38])=[CH:21][N:20]=1)([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].CC(O)=O>C1COCC1>[C:12]([C:8]1[C:9]([CH3:11])=[CH:10][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[C:6]([NH:18][C:19]2[N:24]=[C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[S:32]([CH:35]([CH3:36])[CH3:37])(=[O:34])=[O:33])[C:22]([CH3:38])=[CH:21][N:20]=2)[CH:7]=1)#[CH:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 59764535N2-(2-Isopropoxy-4-methyl-5-trimethylsilanylethynyl-phenyl)-5-methyl-N4-[2-(propane-2-sulfonyl)-phenyl]-pyrimidine-2,4-diamine

Product 1

HCID 59764449N2-(5-Ethynyl-2-isopropoxy-4-methyl-phenyl)-5-methyl-N4-[2-(propane-2-sulfonyl)-phenyl]-pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N2-(2-Isopropoxy-4-methyl-5-trimethylsilanylethynyl-phenyl)-5-methyl-N4-[2-(propane-2-sulfonyl)-phenyl]-pyrimidine-2,4-diamine from the previous step (0.102 g, 0.18 mmol) in 2.5 mL THF is treated with TBAF (0.5 mL, 1M in THF) and 30 μL AcOH at 22° C. for 2 hrs. The reaction mixture is concentrated and the residue is purified using a 4 g SiO2 column (ISCO), affording N2-(5-Ethynyl-2-isopropoxy-4-methyl-phenyl)-5-methyl-N4-[2-(propane-2-sulfonyl)-phenyl]-pyrimidine-2,4-diamine (257). MS (ES+): 479.2 (MH+).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is purified

Sources & evidence

ORD record
ord-4a134b98bdd149b3985a443f6a463e88
Source dataset
uspto-grants-2013_02
Patent number
US08372858B2

Reaction notes

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