HCID 178497705, compound → HCID 178497706, compound

HRID 1108267Notes

Reaction equation

HRID 1108267 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[NH:24][C:23]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][CH:21]=3)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>C(O)(=O)C.[Pt]=O>[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[NH:24][C:23]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][CH:21]=3)[CH2:15][NH:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 178497705HCID 178497705, compound

Product 1

HCID 178497706HCID 178497706, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of methyl 5-[2-(2-pivaloylamino-4-hydroxypyrido[2,3-d]-pyrimidin-6-yl)ethenyl]pyrrole-2-carboxylate (593 mg, 1.5 mmol) and platinum oxide (68 mg) in glacial acetic acid (200 mL) was stirred overnight under hydrogen (50 psi). The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo. The solid was recrystallized from methanol to give methyl 5-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]pyrrole-2-carboxylate as an off-white solid (505 mg, 84%), mp 246-248° C.: 1H NMR (DMSO-d6) δ 11.67 (s, I H), 10.90 (br s, 1H), 10.60 (br s, 1H), 6.66 (s, 1H), 6.45 (s, 1H), 5.91 (s, 1H), 3.72 (s, 3H), 3.22 (brd, 1H, J=10.5 Hz), 2.81 (m, 1H), 2.64 (m, 2H), 2.52 (brd, 1H, J=15.2 Hz), 1.88 (dd, 1H, J=15.2, 7.9 Hz), 1.68-1.50 (m, 3H), 1.21 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe solid was recrystallized from methanol

Sources & evidence

ORD record
ord-0f79496baf634616a9f6a9987ccb5663
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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