HCID 178497680, compound → HCID 178497681, compound

HRID 1108265Notes

Reaction equation

HRID 1108265 reaction equation
[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:39])[C:11]2[CH:17]=[C:16]([C:18]#[C:19][C:20]3[CH:21]=[C:22]([C:35]([O:37][CH3:38])=[O:36])[N:23]([Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH:24]=3)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>CO.[Pd]>[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:39])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([C:35]([O:37][CH3:38])=[O:36])[N:23]([Si:25]([CH:29]([CH3:30])[CH3:31])([CH:26]([CH3:27])[CH3:28])[CH:32]([CH3:34])[CH3:33])[CH:24]=3)[CH2:15][NH:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:4])([CH3:5])[CH3:3]

Participants

4

Reactant 1

HCID 178497680HCID 178497680, compound

Product 1

HCID 178497681HCID 178497681, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 4-[2-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)ethynyl]-1-triisopropylsilylpyrrole-2-carboxylate (550 mg, 1.0 mmol) and 10% palladium-on-carbon (220 mg) in methanol (45 mL) was stirred overnight under hydrogen (50 psi). The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo. The residue was dissolved in methylene chloride and filtered through a short silica gel column. The eluate was evaporated to give methyl 4-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]-1-triisopropylsilylpyrrole-2-carboxylate (524 mg, 94%). The analytical sample, mp 202-204° C., was obtained by column chromatography using chloroform:methanol (19:1): 1H NMR (CDCl3) δ 11.34 (br s, 1H), 7.85 (br s, 1H), 6.98 (s, 1H), 6.90 (s, 1H), 4.69 (s, 1H), 3.79 (s, 3H), 3.36 (br d, 1H, J=10.0 Hz), 2.99 (m, 1H), 2.83 (m, 1H), 2.59 (m, 2H), 2.12 (dd, 1H, J=15.6, 9.0 Hz), 1.90-1.50 (m, 6H), 1.30 (s, 9H), 1.11 (d, 18H, J=7.6 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in methylene chloride
  4. filtrationfiltered through a short silica gel column
  5. customThe eluate was evaporated

Sources & evidence

ORD record
ord-79bab5c82e024e24864ebc4917b36854
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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