Methyl pyruvate → 8-(4-methoxy-2-methyl-phenyl)-4-(1-methoxymethyl-propyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH:16]([CH2:19][O:20][CH3:21])[CH2:17][CH3:18])[C:10]=2[NH2:22])=[C:5]([CH3:23])[CH:4]=1.[C:24](OC)(=[O:28])[C:25]([CH3:27])=O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[N:22]=[C:25]([CH3:27])[C:24](=[O:28])[N:15]([CH:16]([CH2:19][O:20][CH3:21])[CH2:17][CH3:18])[C:11]=3[N:12]=[CH:13][CH:14]=2)=[C:5]([CH3:23])[CH:4]=1Participants
3
Procedure
4-(4-Methoxy-2-methyl-phenyl)-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamine (0.08 g, 0.25 mmol) and methyl pyruvate (33 μL, 0.38 mmol) were treated substantially as in Part E of Example 67a to give 3.0 mg of 8-(4-methoxy-2-methyl-phenyl)-4-(1-methoxymethyl-propyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one (Example 74a): 1H NMR (400 MHz, CDCl3) δ ppm 8.46 (d, J=4.89 Hz, 1 H), 7.15 (d, J=8.31 Hz, 1 H), 7.12 (d, J=4.40 Hz, 1 H), 6.85 (d, J=6.60 Hz, 1 H), 6.83 (d, J=12.23 Hz, 1 H), 5.89 (m, 1 H), 4.38 (m, 1 H), 3.86 (s, 3 H), 3.77 (m, 1 H), 3.32 (s, 3 H), 2.46 (s, 3 H), 2.11 (s, 3 H), 1.77 (m, 2 H), 0.86 (t, J=7.34 Hz, 2 H). MS (EI) 368.30 [(M+H)+, 100]
Sources & evidence
- ORD record
- ord-e6494d544cc348e89d5b02e19cb5950c
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067658B2
Reaction notes
Loading…