(S)-tert-Butyl 3-(2-amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)prop-2-ynylcarbamate → (S)-tert-Butyl 3-(2-amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)propylcarbamate

HRID 2387794Notes

Reaction equation

HRID 2387794 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:10][CH2:11][OH:12])[C:5]([C:17]#[C:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:4]([CH3:28])[N:3]=1>CCO.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:10][CH2:11][OH:12])[C:5]([CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:4]([CH3:28])[N:3]=1

Participants

4

Reactant 1

HCID 86633395(S)-tert-Butyl 3-(2-amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)prop-2-ynylcarbamate

Product 1

HCID 86633396(S)-tert-Butyl 3-(2-amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)propylcarbamateYield 75.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product from step (vii) (100 mg) and Pd/C (30 mg) in EtOH (5 mL) were hydrogenated under 3 bar at rt for 16 h. The catalyst was filtered off and the solvent evaporated to give the subtitle compound 76 mg.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-73a05704fab1480b9356f0fe29657f48
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

Loading…