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

HRID 1375420Notes

Reaction equation

HRID 1375420 reaction equation
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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-4be740f3229043b18e7d5db8aea88064
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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