6-Isopropoxypyrimidine-2,4-diamine → 2-Amino-4-isopropoxy-7-methyl-5-(9-oxo-9H-fluoren-4-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile

HRID 1947253Notes

Reaction equation

HRID 1947253 reaction equation
O=[C:2]([CH3:21])[C:3](=[CH:6][C:7]1[C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:20])[C:11]=2[CH:10]=[CH:9][CH:8]=1)[C:4]#[N:5].[CH:22]([O:25][C:26]1[N:31]=[C:30]([NH2:32])[N:29]=[C:28]([NH2:33])[CH:27]=1)([CH3:24])[CH3:23]>C(O)(C)C>[NH2:32][C:30]1[N:31]=[C:26]([O:25][CH:22]([CH3:24])[CH3:23])[C:27]2[CH:6]([C:7]3[C:19]4[C:18]5[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=5)[C:12](=[O:20])[C:11]=4[CH:10]=[CH:9][CH:8]=3)[C:3]([C:4]#[N:5])=[C:2]([CH3:21])[NH:33][C:28]=2[N:29]=1

Participants

4

Reactant 2

HCID 591869186-Isopropoxypyrimidine-2,4-diamineHCID 674179733-Oxo-2-[(9-oxo-9H-fluoren-4-yl)methylene]butanenitrile

Product 1

HCID 248577482-Amino-4-isopropoxy-7-methyl-5-(9-oxo-9H-fluoren-4-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

81 mg (0.29 mmol) of 3-oxo-2-[(9-oxo-9H-fluoren-4-yl)methylene]butanenitrile are dissolved with 50 mg (0.29 mmol) of 6-isopropoxypyrimidine-2,4-diamine in 5 ml of isopropanol and heated under reflux under argon for 6 h. The suspension is cooled and then filtered with suction, and the remaining solid is washed with isopropanol. 74 mg (59% of theory) of the title compound are obtained as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 6 h
  3. temperatureThe suspension is cooled
  4. filtrationfiltered with suction
  5. washthe remaining solid is washed with isopropanol

Sources & evidence

ORD record
ord-abdf8466e53446abb06378a23a9ec4d8
Source dataset
uspto-grants-2013_03
Patent number
US08399471B2

Reaction notes

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