反応 #1129256

反応方程式

tert-butyl bromoacetate

solution

3-(7-amino-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-1-cyclopentylprop-2-yn-1-ol

NaH

→

title Compound

収率 21.0%

{[3-(7-amino-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-1-cyclopentylprop-2-ynyl]oxy}acetic acid

収率 21.0%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他The reaction mixture was then partitioned between ethyl acetate (10 mL) and brine (10 mL)
3. 3
   乾燥the organic layer was dried over MgSO4
4. 4
   ろ過filtered
5. 5
   その他evaporated to dryness in vacuuo
6. 6
   workup.ADDITIONThe residue was treated with 1.0 mL of 4N HCl in 1,4-dioxane for 3 h
7. 7
   その他Organic solvent was then removed on a rotavap
8. 8
   その他the residue was purified
9. 9
   洗浄eluting with a 5-100% CH3CN gradient in 10 mM ammonium acetate(aq.))

実験手順

To a stirring solution of Example 35B (20 mg, 0.074 mmol) in 0.5 mL of anhydrous N,N-dimethylformamide was added NaH (60%, 4.0 mg, 0.096 mmol). The resulting mixture was stirred for 20 min before tert-butyl bromoacetate (11 μL, 0.0.74 mmol) was added, and stirring continued for 2 h. The reaction mixture was then partitioned between ethyl acetate (10 mL) and brine (10 mL), the organic layer was dried over MgSO4, filtered, evaporated to dryness in vacuuo. The residue was treated with 1.0 mL of 4N HCl in 1,4-dioxane for 3 h. Organic solvent was then removed on a rotavap, and the residue was purified using reverse phase HPLC (C-18 column, eluting with a 5-100% CH3CN gradient in 10 mM ammonium acetate(aq.)) to give the title Compound (5 mg, 21% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.45 (s, 1H), 8.15 (brs, 2H), 4.79-4.60 (m, 2H), 4.34 (d, J=7.1 Hz, 1H), 2.54 (s, 3H), 2.25-2.15 (m, 1H), 1.81-1.38 (m, 8H). MS (ESI) m/z 330 (M+H)+.

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