反応 #60641

反応方程式

[4-(2-amino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(3-nitro-phenyl)-amine

methylsulfonyl chloride

Et3N

→

title compound

N-{4-Methyl-5-[2-(3-nitro-phenylamino)-pyrimidin-4-yl]-thiazol-2-yl}-methane sulfonamide

溶媒

DMF

EtOAc

反応条件

後処理

1. 1
   温度After cooling
2. 2
   洗浄washed with brine
3. 3
   乾燥dried over MgSO4
4. 4
   その他The solvent was evaporated
5. 5
   その他the residue was purified by preparative RP-HPLC
6. 6
   その他over 40 min

実験手順

A mixture of [4-(2-amino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(3-nitro-phenyl)-amine (1.0 mmol, 0.33 g) and methylsulfonyl chloride (2.0 mmol, 0.22 g) in dry DMF (2 mL) was added Et3N (0.28 mL). The reaction mixture was stirred at room temperature for 20 h. After cooling, the mixture was diluted with EtOAc, washed with brine, and dried over MgSO4. The solvent was evaporated and the residue was purified by preparative RP-HPLC using a gradient from 10-70% MeCN in 0.1% aq CF3COOH over 40 min. The title compound was obtained as an orange solid. Anal. RP-HPLC: tR=17.4 min (0-60% MeCN in 0.1% aq CF3COOH over 20 min, 1 mL/min, purity >97%). 1H-NMR (DMSO-d6) δ: 3.10 (s, 3H, CH3), 3.25 (s, 3H, CH3), 7.05 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 7.42 (m, 1H, Ph-H), 7.63 (m, 1H, Ph-H), 7.98 (m, 1H, Ph-H), 8.21 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 8.42 (s, 1H, Ph-H), 9.18 (s, 1H, NH).

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