1,10-Phenanthroline → HCID 57462505, compound

HRID 2241896Notes

Reaction equation

HRID 2241896 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[C:5]2[C:11](=[O:12])[NH:10][C@@H:9]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3Br)[CH2:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[CH:42]1([OH:47])[CH2:46][CH2:45][CH2:44][CH2:43]1>[Cu]I>[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[C:5]2[C:11](=[O:12])[NH:10][C@@H:9]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[O:47][CH:42]3[CH2:46][CH2:45][CH2:44][CH2:43]3)[CH2:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 13181,10-PhenanthrolineHCID 7298CyclopentanolHCID 10796Cesium carbonateHCID 57424845HCID 57424845, compound

Product 1

HCID 57462505HCID 57462505, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
180 °C

Procedure

A microwave vial was charged with (R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one, cesium carbonate (2 eq), copper (I) iodide (10 mol %), 1,10-phenanthroline (20 mol %), and cyclopentanol. The reaction mixture was heated with microwave irradiation to a temperature of 180° C. for 20 min. After cooling to RT, the reactionmixture was concentrated and purified by reverse phase HPLC to afford (R)-2-amino-7-(2-(cyclopentyloxy)-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one (m/z=357 (M+H)).

Workup

  1. temperatureAfter cooling to RT
  2. concentrationthe reactionmixture was concentrated
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-83614e75df9646ecbd7d321b93590249
Source dataset
uspto-grants-2010_03
Patent number
US07671059B2

Reaction notes

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