HCID 178418361, compound → HCID 178497683, compound

HRID 1108268Notes

Reaction equation

HRID 1108268 reaction equation
[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:29])[C:11]2[CH:17]=[C:16]([CH:18]=[CH:19][C:20]3[CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[NH:23][CH:24]=3)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[H][H]>[Pd]>[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:29])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[NH:23][CH:24]=3)[CH2:15][NH:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178497682HCID 178497682, compound

Product 1

HCID 178497683HCID 178497683, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Upon reduction of methyl 4-[2-(2-pivaloylamino-4-hydroxypyrido[2,3-d]-pyrimidin-6-yl)ethenyl]pyrrole-2-carboxylate with hydrogen and palladium-on-carbon catalyst (200 mg) analogously to that described in Example 8, there is obtained methyl 4-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]pyrrole-2-carboxylate (380 mg, 95%): mp 236-238° C.: 1H NMR (DMSO-d6) δ 11.59 (s, 1H), 11.21 (s, 1H), 10.60 (s, 1H), 6.81 (s, 1H), 6.62 (s, 1H), 6.42 (s, 1H), 3.70 (s, 3H), 3.23 (br d, 1H, J=10.5 Hz), 2.82 (m, 1H), 2.57-2.43 (m, 3H), 1.87 (dd, 1H, J=15.2, 8.0 Hz), 1.68-1.43 (m, 3H), 1.18 (s, 9H).

Sources & evidence

ORD record
ord-30d81bed498043699f10d4da78e61bcd
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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