Dichloromethane → 6-Ethoxy-2[3-methoxy-1(2-methoxy-ethyl)-propylamino]-8,8a-dihydro-4aH-pyrido[2,3-d]pyrimidin-7-one

HRID 459907Notes

Reaction equation

HRID 459907 reaction equation
C(S([C:8]1[N:9]=[CH:10][C:11]2[CH:17]=[C:16]([O:18][CH2:19][CH3:20])[C:15](=[O:21])[NH:14][C:12]=2[N:13]=1)(=O)=O)CCC.[CH3:22][O:23][CH2:24][CH2:25][CH:26]([NH2:31])[CH2:27][CH2:28][O:29][CH3:30].C(Cl)Cl.C(Cl)Cl.CO.CC(C)=O>ClCCCl>[CH2:19]([O:18][C:16]1[C:15](=[O:21])[NH:14][CH:12]2[N:13]=[C:8]([NH:31][CH:26]([CH2:27][CH2:28][O:29][CH3:30])[CH2:25][CH2:24][O:23][CH3:22])[N:9]=[CH:10][CH:11]2[CH:17]=1)[CH3:20]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 21584259acetone MeOH DCMHCID 219560502-(Butane-1-sulfonyl)-6-ethoxy-8H-pyrido[2,3-d]pyrimidin-7-oneHCID 859383663-Methoxy-1-(2-methoxy-ethyl)propylamine

Product 1

HCID 219560496-Ethoxy-2[3-methoxy-1(2-methoxy-ethyl)-propylamino]-8,8a-dihydro-4aH-pyrido[2,3-d]pyrimidin-7-oneYield 44.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of compound 3B (50 mg, 0.16 mmol) and 3-methoxy-1-(2-methoxy-ethyl)-propylamine (140 mg, 0.96 mmol) in 1 ml DCE was heated to 85° C. for 72 hours. The reaction mixture was chromographed directly on a Supelco™ 2 g/12 ml silica column with gradient solvent of CH2Cl2 to a final solvent mixture of CH2Cl2:MeOH:acetone (94:3:3). Two additional chromatographies were required to provide 24 mg of 6-Ethoxy-2[3-methoxy-1 (2-methoxy-ethyl)-propylamino]-8,8a-dihydro-4aH-pyrido[2,3-d]pyrimidin-7-one (Example 1) at 86% purity as judged by MS/HPLC. M++337.

Sources & evidence

ORD record
ord-3fd906e1a4ed4d189e307b634c391650
Source dataset
uspto-grants-2007_03
Patent number
US07196097B2

Reaction notes

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