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Acetic Acid → 2-(4-(ethyl((tetrahydrofuran-2-yl)methyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol

HRID 1930665
ノート
印刷プレビュー

反応式

HRID 1930665 の反応式
[CH2:1]([N:3]([CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][O:28]1)[C:4]1[C:5]2[CH2:25][NH:24][CH2:23][CH2:22][C:6]=2[N:7]=[C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:21][CH:20]=[N:19][CH:18]=3)=[CH:13][CH:12]=2)[N:9]=1)[CH3:2].[C:32](O)(=[O:34])[CH3:33].C(O)C=O.C([BH3-])#N.[Na+]>CO>[CH2:1]([N:3]([CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][O:28]1)[C:4]1[C:5]2[CH2:25][N:24]([CH2:33][CH2:32][OH:34])[CH2:23][CH2:22][C:6]=2[N:7]=[C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[O:21][CH:20]=[N:19][CH:18]=3)=[CH:15][CH:16]=2)[N:9]=1)[CH3:2]
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 4

HCID 176Acetic AcidHCID 756GlycolaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59333759N4-Ethyl-N2-(4-(oxazol-5-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

生成物 1

HCID 461997412-(4-(ethyl((tetrahydrofuran-2-yl)methyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol
収率 38.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

N4-Ethyl-N2-(4-(oxazol-5-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (125 mg, 0.30 mmol) was dissolved in methanol (3 mL). Acetic acid (0.017 mL, 0.30 mmol) was added followed by glycoaldehyde (17.85 mg, 0.30 mmol). The reaction mixture was stirred for 15 minutes at room temperature and sodium cyanoborohydride (18.68 mg, 0.30 mmol) (MP—CNBH3) was added. The reaction was stirred overnight at room temperature, the MP—CNBH3 was filtered off, the solvent was evaporated under reduced pressure and the crude was purified by preparative HPLC yielding 2-(4-(ethyl((tetrahydrofuran-2-yl)methyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol (54.0 mg, 34.6%) as acetate salt. MS (ES+) m/z 465.3 (M+H)+

後処理

  1. stirringThe reaction was stirred overnight at room temperature
  2. filtrationthe MP—CNBH3 was filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. customthe crude was purified by preparative HPLC

出典と根拠

ORDレコード
ord-a086a588550b47f0ae6659fc0ff0af91
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08188101B2

反応ノート

読み込み中…

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