Sulfuric acid magnesium salt (1:1) → HCID 86752389, compound

HRID 324701Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6]([CH:8]=[S:9])[CH:5]=[CH:4][N:3]=1.[C:10]([O:14][C:15]([N:17]1CCC(N)CC1)=O)([CH3:13])([CH3:12])[CH3:11].[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[C:10]([O:14][C:15](=[NH:17])[N:3]1[CH2:2][CH2:8][CH:6]([NH2:7])[CH2:5][CH2:4]1)([CH3:13])([CH3:12])[CH3:11].[CH3:1][C:2]1[N:7]=[C:6]([CH:8]=[S:9])[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 23 °C

Procedure

2-Methylthiopyrimidine-4-carboxaldehyde (1.51 g, 9.8 mmol), 1-t-butoxycarbonyl-4-aminopiperidine (Mach R. H., et al., J. Med. Chem. 1993 36, 3707) (2.1 g, 10.5 mmol), MgSO4 (ca 2 g) and CH2Cl2 (75 mL) were combined and stirred at 23° C. for 16 h. Filtration and concentration of the filtrate afforded the title compound as a yellow oil: 1H NMR (CDCl3) δ8.57 (d, 1), 8.27 (s, 1), 7.58 (d, 1), 4.05 (m, 2), 3.55 (m, 1), 3.00 (m, 2), 2.60 (s, 3), 1.75 (m, 4), 1.48 (s, 9).

Workup

filtrationFiltration and concentration of the filtrate

Sources & evidence

ORD record: ord-40c4ac5565584a82ba845d8e3f4104ce
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218537B1

Reaction notes

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