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Ethanol → (R)-9-(2-Methoxyphenyl)-8-oxo-2-(pyrrolidin-3-ylamino)-8,9-dihydro-7H-purine-6-carboxamide

HRID 2427983
ノート
印刷プレビュー

反応式

HRID 2427983 の反応式
[NH2:1][C:2]1[C:3]([C:30]([O:32]CC)=O)=[N:4][C:5]([NH:17][C@@H:18]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]2)=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16].C(OC([N:42]1CC[C@@H](NC2N=C(C(OCC)=O)C([N+]([O-])=O)=C(NC3C=CC=CC=3OC)N=2)C1)=O)(C)(C)C.[CH2:71]([OH:73])C>[Pd]>[CH3:16][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:8]1[C:71](=[O:73])[NH:1][C:2]2[C:7]1=[N:6][C:5]([NH:17][C@@H:18]1[CH2:22][CH2:21][NH:20][CH2:19]1)=[N:4][C:3]=2[C:30]([NH2:42])=[O:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 702EthanolHCID 86627704(R)-Ethyl 2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 86627705(R)-Ethyl 5-amino-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxy-phenylamino)pyrimidine-4-carboxylate

生成物 1

HCID 24937106(R)-9-(2-Methoxyphenyl)-8-oxo-2-(pyrrolidin-3-ylamino)-8,9-dihydro-7H-purine-6-carboxamide収率 89%

試薬・触媒・溶媒

1
HCID 23938Palladium触媒

実験手順

(R)-Ethyl 5-amino-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxy-phenylamino)pyrimidine-4-carboxylate. (R)-Ethyl 2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (0.403 g, 0.802 mmol) was dissolved in ethanol (20 mL) and 10% palladium on carbon (0.080 g) were added to the flask and flushed with fresh hydrogen gas and allowed to stir at room temperature. After 16 hours, the reaction was filtered through celite and the filtrate condensed under reduced pressure. The crude oil was purified using biotage chromatography (0-100% ethyl acetate in hexanes) to afford the title compound (0.340 g, 89%). MS (ESI) m/z 473.5 [M+1]+.

後処理

  1. customflushed with fresh hydrogen gas
  2. filtrationthe reaction was filtered through celite
  3. customthe filtrate condensed under reduced pressure
  4. customThe crude oil was purified

出典と根拠

ORDレコード
ord-85299183c7714f2fa5500908dc0755b0
出典データセット
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07968556B2

反応ノート

読み込み中…

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