반응 #509178

반응 방정식

4-chloro-5-iodo-6-methylpyrimidin-2-amine

triethylamine

4-aminotetrahydropyran HCl salt

→

5-iodo-6-methyl-N4-(tetrahydro-2H-pyran-4-yl)pyrimidine-2,4-diamine

수율 51.7%

용매

EtOH

H2O

반응 조건

후처리

1. 1
   온도The reaction was heated
2. 2
   온도to reflux
3. 3
   기타About 80% of the solvent was evaporated under reduced pressure
4. 4
   기타The mixture was partitioned between ethyl acetate and H2O
5. 5
   건조The organic layer was dried over anhydrous sodium sulfate
6. 6
   농축concentrated in vacuo
7. 7
   기타to afford the crude product
8. 8
   기타The product was purified by a flash chromatography (50% ethyl acetate/hexanes to 100% ethyl acetate)

실험 절차

To a suspension of 4-chloro-5-iodo-6-methylpyrimidin-2-amine (16.0 g, 59.3 mmol) in EtOH (200 mL) and H2O (250 mL) was added triethylamine (30.0 mL, 207.5 mmol) and 4-aminotetrahydropyran HCl salt (9.75 g, 71.2 mmol) successively. The reaction was heated to reflux, stirred for 72 h, and then cooled to RT. About 80% of the solvent was evaporated under reduced pressure. The mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to afford the crude product. The product was purified by a flash chromatography (50% ethyl acetate/hexanes to 100% ethyl acetate) to afford 5-iodo-6-methyl-N4-(tetrahydro-2H-pyran-4-yl)pyrimidine-2,4-diamine as a light yellow crystal (yield: 10.23 g, 51.7%). LC/MS: calculated for C10H15IN4O (334.03). found: 335.08 (MH+). HPLC analytical purity: >99.0%.

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