Ethanol → 4-(4-{4-amino-7,7-dimethyl-7H-pyrimido[4,5-b][1,4]oxazin-6-yl}phenyl)bicyclo[2.2.2]octane-1-carboxylic acid

HRID 908124ノート

反応式

HRID 908124 の反応式
[NH2:1][C:2]1[C:11]2[N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([C:18]45[CH2:25][CH2:24][C:21]([C:26]([O:28]C)=[O:27])([CH2:22][CH2:23]4)[CH2:20][CH2:19]5)=[CH:14][CH:13]=3)[C:8]([CH3:31])([CH3:30])[O:7][C:6]=2[N:5]=[CH:4][N:3]=1.[OH-].[Na+].CCO>CO>[NH2:1][C:2]1[C:11]2[N:10]=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([C:18]45[CH2:23][CH2:22][C:21]([C:26]([OH:28])=[O:27])([CH2:20][CH2:19]4)[CH2:24][CH2:25]5)=[CH:16][CH:17]=3)[C:8]([CH3:31])([CH3:30])[O:7][C:6]=2[N:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 702EthanolHCID 14798Sodium Hydroxide2 回HCID 25258106methyl 4-[4-(4-amino-7,7-dimethyl-7H-pyrimido[4,5-b][1,4]oxazin-6-yl)phenyl]bicyclo[2.2.2]octane-1-carboxylate2 回

生成物 1

HCID 250164264-(4-{4-amino-7,7-dimethyl-7H-pyrimido[4,5-b][1,4]oxazin-6-yl}phenyl)bicyclo[2.2.2]octane-1-carboxylic acid収率 724.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of methyl 4-[4-(4-amino-7,7-dimethyl-7H-pyrimido[4,5-b][1,4]oxazin-6-yl)phenyl]bicyclo[2.2.2]octane-1-carboxylate (Intermediate 27; 140 mg, 0.33 mmol) in MeOH (10 mL) was added 2M NaOH (0.82 mL, 1.66 mmol). The reaction mixture was allowed to stir at ambient temperature overnight and then after the addition of EtOH (˜5 mL) and 1M NaOH (2 mL) the reaction mixture was heated to 50° C. for 5.5 hrs. The organic solvent was removed by evaporation under reduced pressure and the residue was acidified to pH 2 with 2M HCl. EtOAc was added and the suspension was filtered and dried to provide the title compound (97 mg, 2.39 mmol, 72%); 1H NMR δ 1.60 (s, 6H), 1.82 (s, 12H), 6.97 (s, 1H), 7.40 (d, 2H), 7.65 (d, 2H), 7.95 (s, 1H), NH2 not seen; MS m/e MH+ 407.

後処理

  1. temperaturewas heated to 50° C. for 5.5 hrs
  2. customThe organic solvent was removed by evaporation under reduced pressure
  3. additionEtOAc was added
  4. filtrationthe suspension was filtered
  5. customdried

出典と根拠

ORDレコード
ord-741dfe5e71174cd5a48833074dae8505
出典データセット
uspto-grants-2011_09
特許番号
US08017603B2

反応ノート

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