Ethanol → 2-(2-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 2428016노트

반응식

HRID 2428016 반응식
[NH2:1][C:2]1[C:3]([C:26](OCC)=[O:27])=[N:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:24][OH:25])=[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(C1C([N+]([O-])=O)=C(NC2C=CC=CC=2OC)N=C(NC2C=CC=CC=2CO)[N:37]=1)=O)C.[CH2:63]([OH:65])C>[Pd]>[OH:25][CH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:5]1[N:6]=[C:7]2[C:2]([NH:1][C:63](=[O:65])[N:8]2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:3]([C:26]([NH2:37])=[O:27])[N:4]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 57474717Ethyl 5-nitro-2-(2-(hydroxymethyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylateHCID 57474718Ethyl 5-amino-2-(2-(hydroxymethyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate

생성물 1

HCID 574747162-(2-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide수율 89%

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

Ethyl 5-amino-2-(2-(hydroxymethyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. Ethyl-5-nitro-2-(2-(hydroxymethyl)phenylamino)-6-(2-methoxy-phenylamino)pyrimidine-4-carboxylate (0.325 g, 0.740 mmol) was dissolved in ethanol (20 mL) and 10% palladium on carbon (0.081 g) were added to the flask and flushed with fresh hydrogen gas and allowed to stir at room temperature. After 16 h, the reaction was filtered through celite and the filtrate condensed under reduced pressure. The crude oil was purified using biotage chromatography (50-100% ethyl acetate in hexanes) to afford the title compound (0.270 g., 89%). MS (ESI) m/z 410.5 [M+1]+.

후처리

  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

출처 및 근거

ORD 기록
ord-100faea75c1846dc97618ad5602b4ffa
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968556B2

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