(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 1617141Notes

Reaction equation

HRID 1617141 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-e9ada8e45a29462e8b5b9c5cbeb8da59
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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