2,4-Diamino-6-ethoxypyrimidine → 8-(6-Acetyl-2-amino-4-ethoxy-7-methyl-5,8-dihydropyrido[2,3-d]pyrimidin-5-yl)-2-methyl-4H-chromen-4-one

HRID 1947251Notes

Reaction equation

HRID 1947251 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=[C:14]([C:18](=[O:20])[CH3:19])[C:15](=O)[CH3:16].[CH2:21]([O:23][C:24]1[N:29]=[C:28]([NH2:30])[N:27]=[C:26]([NH2:31])[CH:25]=1)[CH3:22]>C(O)(C)C>[C:18]([C:14]1[CH:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:25]2[C:24]([O:23][CH2:21][CH3:22])=[N:29][C:28]([NH2:30])=[N:27][C:26]=2[NH:31][C:15]=1[CH3:16])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 2226632,4-Diamino-6-ethoxypyrimidineHCID 591869153-[(2-Methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione

Product 1

HCID 248577468-(6-Acetyl-2-amino-4-ethoxy-7-methyl-5,8-dihydropyrido[2,3-d]pyrimidin-5-yl)-2-methyl-4H-chromen-4-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

270 mg (1 mmol) of 3-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione and 170 mg (1.1 mmol) of 6-ethoxypyrimidine-2,4-diamine are dissolved in 5 ml of isopropanol and heated under reflux under argon for 2 days. The mixture is then concentrated and the residue is purified by preparative HPLC. 230 mg (56% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 2 days
  3. concentrationThe mixture is then concentrated
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-98a7d2bfba15401c99f3629cd15d33ef
Source dataset
uspto-grants-2013_03
Patent number
US08399471B2

Reaction notes

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