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

HRID 362616Notes

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-2f6c2e3147a241fab53cc32c35251fe7
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869660

Reaction notes

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