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Acetic Acid → 2-((2-(4-(Oxazol-5-yl)phenylamino)-6-propyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol

HRID 1930558
ノート
印刷プレビュー

反応式

HRID 1930558 の反応式
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[N:14]=[C:15]([N:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:24][CH2:25][OH:26])[C:16]4[CH2:22][NH:21][CH2:20][CH2:19][C:17]=4[N:18]=3)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.C(O)(=O)C.[CH:37](=O)[CH2:38][CH3:39].C([BH3-])#N.[Na+]>CO>[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[N:14]=[C:15]([N:23]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:24][CH2:25][OH:26])[C:16]4[CH2:22][N:21]([CH2:37][CH2:38][CH3:39])[CH2:20][CH2:19][C:17]=4[N:18]=3)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]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 4

HCID 176Acetic AcidHCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 462000502-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol

生成物 1

HCID 462003542-((2-(4-(Oxazol-5-yl)phenylamino)-6-propyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol収率 22.95%

試薬・触媒・溶媒

1
HCID 887Methanol溶媒

実験手順

2-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (25 mg, 0.06 mmol, Example 1) was dissolved in methanol (1 mL). Acetic acid (0.013 mL, 0.23 mmol) and propionaldehyde (4.25 μL, 0.06 mmol) was added and the reaction mixture was stirred at room temperature for 10 minutes. Sodium cyanoborohydride (3.67 mg, 0.06 mmol) was added and after 15 minutes the solvent was evaporated under reduced pressure. The crude was dissolved in few drops of dimethylformamide and acetonitrile, filtered and purified by preparative HPLC yielding 2-((2-(4-(oxazol-5-yl)phenylamino)-6-propyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (6.3 mg, 22.95%).

後処理

  1. customwas evaporated under reduced pressure
  2. dissolutionThe crude was dissolved in few drops of dimethylformamide and acetonitrile
  3. filtrationfiltered
  4. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-00d4f4d907a743ecb22262bd02ed324b
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

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