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Sodium Hydroxide → 5-Benzyloxy-1-methyl-6-oxo-2-p-tolylmethanesulfonyl-amino-1,6-dihydro-pyrimidine-4-carboxylic acid methylamide

HRID 1409594
ノート
印刷プレビュー

反応式

HRID 1409594 の反応式
CC(C)([O-])C.[K+].[NH2:7][C:8]1[N:9]([CH3:27])[C:10](=[O:26])[C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([C:14]([NH:16][CH3:17])=[O:15])[N:13]=1.[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][S:36](Cl)(=[O:38])=[O:37])=[CH:31][CH:30]=1.[OH-].[Na+]>C1COCC1.CN(C=O)C.CCOC(C)=O>[CH3:17][NH:16][C:14]([C:12]1[NH:13][C:8]([NH2:7])([S:36]([CH2:35][C:32]2[CH:33]=[CH:34][C:29]([CH3:28])=[CH:30][CH:31]=2)(=[O:38])=[O:37])[N:9]([CH3:27])[C:10](=[O:26])[C:11]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 2794648(4-Methylphenyl)methanesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 867102892-amino-5-(benzyloxy)-N,1-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

生成物 1

HCID 1317322065-Benzyloxy-1-methyl-6-oxo-2-p-tolylmethanesulfonyl-amino-1,6-dihydro-pyrimidine-4-carboxylic acid methylamide収率 46%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Potassium tert-butoxide (93.8 mg, 836 μmol) was added to a solution of 2-amino-5-(benzyloxy)-N,1-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide (110 mg, 380 μmol) in THF (10 ml) in DMF (2 ml) [Comment: please check]. After 10 min., the reaction mixture was cooled by an ice bath and then a solution of (4-methylphenyl)methanesulfonyl chloride (93.7 mg, 458 μmol) in THF (2 ml) was added. After 70 min., EtOAc and 1 N NaOH aqueous solution were added. The organic phase was extracted with EtOAc and then with DCM. The combined organic phases were washed with water, and brine, dried over Na2SO4 and evaporated to dryness. Chromatography (silica gel, 0 to 2% MeOH in DCM) provided the title compound as a pale yellow solid (0.080 g; 46%). LCMS: m/z=457 (MH+).

後処理

  1. temperaturethe reaction mixture was cooled by an ice bath
  2. waitAfter 70 min.
  3. extractionThe organic phase was extracted with EtOAc
  4. washThe combined organic phases were washed with water, and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-1e416b9e25694165ab4ad6799b502a63
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08921388B2

反応ノート

読み込み中…

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