Methanol → 5-iodo-2-methoxy-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine

HRID 1621517ノート

反応式

HRID 1621517 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[C:5]([I:17])=[CH:4][N:3]=1.[CH3:18][O-:19].[Na+].CO>O>[I:17][C:5]1[C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)=[N:7][C:2]([O:19][CH3:18])=[N:3][CH:4]=1

参加物

5

反応物 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 866470532-chloro-5-iodo-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine

生成物 1

HCID 666002025-iodo-2-methoxy-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine収率 91%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

A glass microwave reaction vessel was charged with 2-chloro-5-iodo-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine (181 mg, 0.499 mmol), sodium methoxide (0.5 M solution in methanol, 0.043 mL, 0.749 mmol) and methanol (1 mL). The reaction mixture was stirred and heated in a Emrys Optimizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 140° C. for 15 min. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2×20 mL). The organic extract was washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a white solid. The crude product was purified by silica gel chromatography eluting with 50% EtOAc/hexanes to give 5-iodo-2-methoxy-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine (162 mg, 0.452 mmol, 91% yield). 1H NMR (300 MHz, CDCl3) δ 8.35 (s, 1H); 8.26 (d, J=2.05 Hz, 1H); 7.83 (dd, J=8.84, 2.56 Hz, 1H); 6.87 (s, 1H); 6.78 (d, J=8.77 Hz, 1H); 3.94 (s, 3H); 3.89 (s, 3H). m/z (ESI, +ve ion) 359.0 (M+H)+.

後処理

  1. customA glass microwave reaction vessel
  2. extractionextracted with EtOAc (2×20 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl (5 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo
  8. customto give the crude material as a white solid
  9. customThe crude product was purified by silica gel chromatography
  10. washeluting with 50% EtOAc/hexanes

出典と根拠

ORDレコード
ord-885ec10879504b14a8aca347123da22b
出典データセット
uspto-grants-2014_07
特許番号
US08772480B2

反応ノート

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