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Acetic Acid → 2-[[4-[4(Tert-butoxycarbonyl)piperazin-1-yl]phenyl]amino]-8-cyclopentyl-8h-pteridin-7-one

HRID 1375421
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HRID 1375421 반응식
[NH2:1][C:2]1[C:3]([NH:28][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[C:34](OCCCC)(=O)[CH:35]=[O:36].CC(O)=O>CCO>[C:24]([O:23][C:21]([N:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:5]3[N:6]=[CH:7][C:2]4[N:1]=[CH:34][C:35](=[O:36])[N:28]([CH:29]5[CH2:30][CH2:31][CH2:32][CH2:33]5)[C:3]=4[N:4]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17]1)=[O:22])([CH3:27])([CH3:26])[CH3:25]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 80521Butyl oxoacetateHCID 587867835-Amino-2-[[4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl]amino]-4-(cyclopentylamino)pyrimidine

생성물 1

HCID 99353632-[[4-[4(Tert-butoxycarbonyl)piperazin-1-yl]phenyl]amino]-8-cyclopentyl-8h-pteridin-7-one수율 43%

시약·촉매·용매 1

HCID 702Ethanol
용매

실험 절차

A mixture of 0.82 g (1.8 mmol) of 5-amino-2-[[4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl]amino]-4-(cyclopentylamino)pyrimidine (from preparation 14A), 0.52 g (4 mmol) of butyl glyoxylate (F. J. Wolf, J. Weijlard, Org. Synth. Coll., 1963;4:124–125), and 0.5 mL HOAc in 15 mL of EtOH is heated under reflux for 14 hours, and the solvent is removed under vacuum. The residue is diluted with aqueous ammonia solution and extracted into EtOAc. Chromatography on silica, eluting with hexane/EtOAc (3:2) gave 0.38 g (43%) of the title compound (Compound 52): mp (MeOH) 215–217° C.

후처리

  1. temperatureis heated
  2. temperatureunder reflux for 14 hours
  3. customthe solvent is removed under vacuum
  4. additionThe residue is diluted with aqueous ammonia solution
  5. extractionextracted into EtOAc
  6. washChromatography on silica, eluting with hexane/EtOAc (3:2)

출처 및 근거

ORD 기록
ord-4e809fc02d4849989c58b13198046607
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07169778B2

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