Tetrabutylammonium Fluoride → 4-[4-(3-Amino-2-fluorophenyl)-2-(1,1-dimethylethyl)-1,3-thiazol-5-yl]-2-pyrimidinamine

HRID 239388Notes

Reaction equation

HRID 239388 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:10][C:9]=2[C:17]2[C:18]([F:30])=[C:19]([NH:23]C(=O)OCC=C)[CH:20]=[CH:21][CH:22]=2)[CH:5]=[CH:4][N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH2:23][C:19]1[C:18]([F:30])=[C:17]([C:9]2[N:10]=[C:11]([C:13]([CH3:15])([CH3:14])[CH3:16])[S:12][C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=2)[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 579896502-Propen-1-yl {3-[5-(2-amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}carbamate

Product 1

HCID 579897094-[4-(3-Amino-2-fluorophenyl)-2-(1,1-dimethylethyl)-1,3-thiazol-5-yl]-2-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-propen-1-yl {3-[5-(2-amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}carbamate (220 mg, 0.515 mmol) in TBAF (1 mL, 1.0 mmol) in 1M THF was heated in a microwave reactor at 130° C. for 10 min. The crude reaction mixture was evaporated onto silica gel and chromatographed (1:9:90 NH4OH:MeOH:DCM in DCM 10-80%). The title compound was obtained as a white solid (100 mg, 56% yield). MS (ESI): 344.1 [M+H]+.

Workup

  1. customThe crude reaction mixture
  2. customwas evaporated onto silica gel
  3. customchromatographed (1:9:90 NH4OH:MeOH:DCM in DCM 10-80%)

Sources & evidence

ORD record
ord-7704b89402ad451a8e13d038d912073a
Source dataset
uspto-grants-2014_02
Patent number
US08642759B2

Reaction notes

Loading…