4-(2-(Diethylamino)ethoxy)aniline → HCID 5330243, compound

HRID 2300062Notes

Reaction equation

HRID 2300062 reaction equation
[CH:1]([N:4]1[C:9]2[N:10]=[C:11](S(C)=O)[N:12]=[CH:13][C:8]=2[CH:7]=[CH:6][C:5]1=[O:17])([CH3:3])[CH3:2].[CH2:18]([N:20]([CH2:31][CH3:32])[CH2:21][CH2:22][O:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)[CH3:19]>>[CH2:31]([N:20]([CH2:18][CH3:19])[CH2:21][CH2:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([NH:28][C:11]2[N:12]=[CH:13][C:8]3[CH:7]=[CH:6][C:5](=[O:17])[N:4]([CH:1]([CH3:3])[CH3:2])[C:9]=3[N:10]=2)=[CH:29][CH:30]=1)[CH3:32]

Participants

3

Reactant 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 10705897HCID 10705897, compound

Product 1

HCID 5330243HCID 5330243, compoundYield 47.5%

Conditions

Temperature
175 °C

Procedure

To 8-isopropyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (126 mg, 0.50 mmol) was added 4-(2-diethylaminoethoxy)aniline (313 mg, 1.51 mmol). The reaction mixture was heated at 175° C. for 10 minutes then cooled to room temperature and partitioned between saturated sodium bicarbonate and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography eluting with 10% methanol in ethyl acetate. The fractions containing product were concentrated, and hexane was added. The resultant solid was collected by filtration to give 94 mg (47%) of 2-[4-(2-diethylaminoethoxy)-phenylamino]-8-isopropyl-8H-pyrido[2,3-d]pyrimidin-7-one, mp 84-85° C.

Workup

  1. temperaturethen cooled to room temperature
  2. custompartitioned between saturated sodium bicarbonate and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting with 10% methanol in ethyl acetate
  8. additionThe fractions containing product
  9. concentrationwere concentrated
  10. additionhexane was added
  11. filtrationThe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-05ad1b6f978d4c5fb0e3d37d2c5a8724
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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