Acetic Acid → 8-Cyclopentyl-2-[[4-(morpholin-4-yl)phenyl]amino]-8H-pteridin-7-one

HRID 1375420

反応式

HRID 1375420 の反応式
N1C=[CH:5][CH:4]=[N:3][CH:2]=1.[NH2:7][C:8]1[C:9]([NH:29][CH2:30][CH3:31])=[N:10][C:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18](OCCN(CC)CC)=[CH:17][CH:16]=2)=[N:12][CH:13]=1.COC1C=[C:36]([C:42](=O)[C:43](OCC)=O)[CH:37]=[C:38](OC)C=1.[C:49](O)(=[O:51])C.CC[OH:55]>>[CH:36]1([N:29]2[C:9]3[N:10]=[C:11]([NH:14][C:15]4[CH:16]=[CH:17][C:18]([N:3]5[CH2:2][CH2:49][O:51][CH2:5][CH2:4]5)=[CH:19][CH:20]=4)[N:12]=[CH:13][C:8]=3[N:7]=[CH:31][C:30]2=[O:55])[CH2:37][CH2:38][CH2:43][CH2:42]1

参加物

5

反応物 4

HCID 176Acetic AcidHCID 702EthanolHCID 24722256Ethyl (3,5-dimethoxyphenyl)(oxo)acetateHCID 694755325-Amino-2-[[4-[2-(diethylamino)-ethoxy]phenyl]amino]-4-(ethylamino)pyrimidine pyrimidine

生成物 1

HCID 98653148-Cyclopentyl-2-[[4-(morpholin-4-yl)phenyl]amino]-8H-pteridin-7-one収率 56%

実験手順

A mixture of 0.96 g (2.8 mmol) of 5-amino-2-[[4-[2-(diethylamino)-ethoxy]phenyl]amino]-4-(ethylamino)pyrimidine pyrimidine, 0.83 g (35 mmol) of ethyl 2-(3,5-dimethoxyphenyl)-2-oxoacetate (from Example 4(2)), and 1 mL of acetic acid in 25 mL EtOH is heated under reflux for 14 hours, and the solvent is removed under vacuum. The residue is then dissolved in water and washed with EtOAc. The aqueous layer is made basic with aqueous ammonia, and the crude product is extracted into fresh EtOAc. Chromatography on alumina, eluting with hexane/EtOAc (1:1), then gives 0.81 g (56%) of the title compound (Compound 14): mp (MeOH) 154–155° C.

後処理

  1. temperatureis heated
  2. temperatureunder reflux for 14 hours
  3. customthe solvent is removed under vacuum
  4. dissolutionThe residue is then dissolved in water
  5. washwashed with EtOAc
  6. extractionthe crude product is extracted into fresh EtOAc
  7. washChromatography on alumina, eluting with hexane/EtOAc (1:1)

出典と根拠

ORDレコード
ord-4be740f3229043b18e7d5db8aea88064
出典データセット
uspto-grants-2007_01
特許番号
US07169778B2

関連ノート

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