反応 #679524

反応方程式

1-Boc-4-(4-aminophenyl)piperidine

Et2O

2,4-Dichloro-5-(trifluoromethyl)pyrimidine

Et3N

→

title compound

tert-Butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

溶媒

DCE

t-BuOH

反応条件

後処理

1. 1
   その他at room temperature
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITcontinued at room temperature overnight
4. 4
   その他The volatiles were evaporated to dryness
5. 5
   その他After sonication for 30 minutes the suspension
6. 6
   ろ過was filtered
7. 7
   洗浄the filter cake was washed with water (2×100 mL)
8. 8
   その他dried under a high vacuum

実験手順

2,4-Dichloro-5-(trifluoromethyl)pyrimidine (4.122 g, 19.00 mmol) was stirred in a 1:1 t-BuOH:DCE mixture (400 mL) at room temperature. A 1.0 M ZnCl2 solution in Et2O (21.71 mL, 21.71 mmol) was added cautiously and the resulting mixture was stirred for 10 minutes. 1-Boc-4-(4-aminophenyl)piperidine (5.00 g, 18.1 mmol) was added followed by Et3N (6.052 mL, 43.42 mmol) and stirring continued at room temperature overnight. The volatiles were evaporated to dryness and the resulting residue was suspended in water (500 mL). After sonication for 30 minutes the suspension was filtered and the filter cake was washed with water (2×100 mL) and dried under a high vacuum to yield the title compound K3 as a tan solid (8.11 g, 98%); 1H NMR (400 MHz, d6-DMSO) δ 10.61 (s, 1H), 8.78 (s, 1H), 7.59 (d, J=8.4 Hz, 2H), 7.23 (d, J=8.5 Hz, 2H), 4.07 (d, J=11.1 Hz, 2H), 2.80 (s, 2H), 2.65 (t, J=12.0 Hz, 1H), 1.74 (d, J=12.3 Hz, 2H), 1.42 (s, 11H). LCMS-A: rt 6.834 min; m/z 457 [M+H]+.

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