5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde → 1-(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanol

HRID 1811984ノート

反応式

HRID 1811984 の反応式
[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][N:8]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[C:17]([NH:24][C:25]4[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=4)=[N:18][CH:19]=[C:20]([CH:23]=3)[CH:21]=[O:22])[N:10]=2)=[CH:5][CH:4]=1.[CH3:44][Mg]Br>C1COCC1>[CH3:41][O:40][C:37]1[CH:36]=[CH:35][C:34]([CH2:33][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:43][CH:42]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:23]=[C:20]([CH:21]([OH:22])[CH3:44])[CH:19]=[N:18][C:17]=3[NH:24][C:25]3[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[N:10]=2)=[CH:39][CH:38]=1

参加物

4

反応物 2

HCID 601552675-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehydeHCID 178418573HCID 178418573、化合物

生成物 1

HCID 666113881-(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanol収率 97.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde (877.5 mg, 1.519 mmol) was suspended in THF (15 mL) and methylmagnesium bromide (3.0 M in diethyl ether, 1.5 mL, 4.5 mmol) was added. More THF (2.5 mL) was added after about 10 min. After 40 additional min, the reaction was quenched with saturated ammonium chloride and diluted with water (20 mL). The layers were separated, and the aqueous phase was extracted with EtOAc. The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified on a silica gel filter (150 mL fritted filter with about 2 inches of silica gel; 100:1 DCM/MeOH to 40:1 DCM/MeOH) to afford 1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanol (878.2 mg). 1H NMR (CDCl3, 400 MHz) δ 11.62 (s, 1H), 8.82 (d, J=2.54 Hz, 1H), 8.30 (d, J=2.54 Hz, 1H), 8.26 (d, J=2.74 Hz, 1H), 7.88 (dd, J=8.80 Hz, 2.74 Hz, 1H), 7.21 (dd, J=12.91 Hz, 8.61 Hz, 4H), 6.90-6.82 (m, 4H), 6.71 (d, J=8.80 Hz, 1H), 4.93-4.86 (m, 3H), 4.82 (d, J=6.26 Hz, 2H), 3.93 (s, 3H), 3.82 (s, 3H), 3.79 (s, 3H), 2.58 (s, 3H), 1.72 (d, J=3.91 Hz, 1H), 1.52 (d, J=6.46 Hz, 3H). m/z (ESI, +ve ion) 594 (M+H)+.

後処理

  1. customAfter 40 additional min, the reaction was quenched with saturated ammonium chloride
  2. additiondiluted with water (20 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified on a silica gel
  9. filtrationfilter (150 mL fritted filter with about 2 inches of silica gel; 100:1 DCM/MeOH to 40:1 DCM/MeOH)

出典と根拠

ORDレコード
ord-d09d38c7c954499a836fc994d2abcbfe
出典データセット
uspto-grants-2013_01
特許番号
US08362241B2

反応ノート

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