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Sodium bis(trimethylsilyl)amide → 1-(5-(4-Amino-6-methyl-1,3,5-triazin-2-yl)-6-(6-chloro-5-methoxypyridin-3-ylamino)pyridin-3-yl)ethanone

HRID 1812377
ノート
印刷プレビュー

反応式

HRID 1812377 の反応式
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:13]2[N:18]=[C:17]([CH3:19])[N:16]=[C:15]([NH2:20])[N:14]=2)[C:9](F)=[N:10][CH:11]=1)=[CH2:5])C.[Cl:21][C:22]1[N:27]=[CH:26][C:25]([NH2:28])=[CH:24][C:23]=1[O:29][CH3:30].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.CN(C=O)C>[NH2:20][C:15]1[N:16]=[C:17]([CH3:19])[N:18]=[C:13]([C:8]2[CH:7]=[C:6]([C:4](=[O:3])[CH3:5])[CH:11]=[N:10][C:9]=2[NH:28][C:25]2[CH:26]=[N:27][C:22]([Cl:21])=[C:23]([O:29][CH3:30])[CH:24]=2)[N:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 234561436-Chloro-5-methoxypyridin-3-amineHCID 666118404-(5-(1-Ethoxyvinyl)-2-fluoropyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

生成物 1

HCID 866470821-(5-(4-Amino-6-methyl-1,3,5-triazin-2-yl)-6-(6-chloro-5-methoxypyridin-3-ylamino)pyridin-3-yl)ethanone収率 64.3%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 4-(5-(1-ethoxyvinyl)-2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (100 mg, 0.363 mmol) and 6-chloro-5-methoxypyridin-3-amine (Small Molecules, Inc) (86 mg, 0.545 mmol) in 1 mL of THF and 0.3 mL of DMF at 0° C. was added sodium bis(trimethylsilyl)amide (1.09 mL of 1.0 M solution in THF, 1.09 mmol) dropwise and the dark red solution was stirred at this temperature for 30 min. It was quenched with 4 mL of 0.5 N HCl and stirred at RT for 10 min. The mixture was treated with 1 N NaOH to pH of about 8. It was extracted twice with EtOAc (30 mL). The combined organic phases were washed with brine and dried over Na2SO4. It was concentrated to half of its volume, the precipitated tan solid was filtered through a fritted funnel, rinsed with 2 mL of ether, collected and dried to give 1-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(6-chloro-5-methoxypyridin-3-ylamino)pyridin-3-yl)ethanone (90 mg, 64% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.63 (s, 1H), 9.29 (s, 1H), 9.03 (s, 1H), 8.47 (s, 1H), 8.30 (s, 1H), 8.06 (br., 1H), 7.90 (br., 1H), 3.96 (s, 3H), 2.60 (s, 3H), 2.47 (s, 3H). m/z (ESI, positive ion) 386.0 (M+H)+.

後処理

  1. customIt was quenched with 4 mL of 0.5 N HCl
  2. stirringstirred at RT for 10 min
  3. additionThe mixture was treated with 1 N NaOH to pH of about 8
  4. extractionIt was extracted twice with EtOAc (30 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationIt was concentrated to half of its volume
  8. filtrationthe precipitated tan solid was filtered through a fritted funnel
  9. washrinsed with 2 mL of ether
  10. customcollected
  11. customdried

出典と根拠

ORDレコード
ord-446094d181d84d7d82bf29111a7711af
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08362241B2

反応ノート

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