1,1'-Carbonyldiimidazole → 5-chloro-3-[(4-methoxyphenyl)methyl]-1H,2H,3H,4H-pyrido[2,3-d]pyrimidin-2-one

HRID 1045485

Reaction equation

HRID 1045485 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[C:15]=1[CH2:21][NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1>C(#N)C>[Cl:13][C:14]1[C:15]2[CH2:21][N:22]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:6](=[O:7])[NH:20][C:16]=2[N:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 669263404-Chloro-3-(((4-methoxybenzyl)amino)methyl)pyridin-2-amine

Product 1

HCID 669262915-chloro-3-[(4-methoxyphenyl)methyl]-1H,2H,3H,4H-pyrido[2,3-d]pyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

CDI (583 mg, 3.56 mmol) was added to a solution of 4-chloro-3-((4-methoxybenzylamino)methyl) pyridin-2-amine (100 mg, 1.19 mmol) in acetonitrile (5 mL), and stirred for 1 h at room temperature. The resulting precipitate was filtered, and washed with H2O and MeOH, to provide 1 as a solid. LC-MS (M+H=303, obsd.=303. 1H NMR: (DMSO-D6) δ 3.74 (s, 3H); 4.34 (s, 2H); 4.52(s, 2H); 6.92 (d, 2H); 7.03 (d, 1H); 7.26 (d, 2H); 8.03 (d, 1H); 10.08 (s, 1H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with H2O and MeOH

Sources & evidence

ORD record
ord-881d9a76868d4effb135007702ae3bd8
Source dataset
uspto-grants-2013_10
Patent number
US08569295B2

Linked notes

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