4,4-Dimethoxy-2-butanone → HCID 76684684, compound

HRID 1752816Notes

Reaction equation

HRID 1752816 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][S:9][C:10]2[N:14]=[C:13]([NH2:15])[NH:12][N:11]=2)=[CH:4][CH:3]=1.CO[CH:20](OC)[CH2:21][C:22](=O)[CH3:23]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][S:9][C:10]2[N:14]=[C:13]3[N:15]=[CH:20][CH:21]=[C:22]([CH3:23])[N:12]3[N:11]=2)=[CH:16][CH:17]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][S:9][C:10]2[N:14]=[C:13]3[N:15]=[C:22]([CH3:23])[CH:21]=[CH:20][N:12]3[N:11]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 2285484,4-Dimethoxy-2-butanoneHCID 1648919HCID 1648919, compound

Product 2

HCID 76684684HCID 76684684, compoundHCID 86719327HCID 86719327, compound

Procedure

The title compound was prepared according to the experimentals described for Example 23 above from 3-{[2-(4-chlorophenoxy)ethyl]sulfanyl}-1H-1,2,4-triazol-5-amine and acetylacetaldehyde dimethyl acetal. The two regioisomers were separated by silica gel chromatography. 2-{[2-(4-chlorophenoxy)ethyl]sulfanyl}-5-methyl-[1,2,4]-triazolo[1,5-a]pyrimidine was obtained as off white crystals in 25% yield: EM (calc.): 320.0; MS (ESI) m/e: 321.0 (M+H)+. 1H NMR (CDCl3, 400 MHz) δ ppm: 8.53 (d, 1H, J=6.8 Hz), 7.22 (d, 2H), 6.90 (d, 1H, J=6.8 Hz), 6.87 (d, 2H), 4.34 (t, 2H), 3.63 (t, 2H), 2.70 (s, 3H).

Workup

  1. customThe two regioisomers were separated by silica gel chromatography

Sources & evidence

ORD record
ord-aaafa5bc537a440493cb5cb41aa3a3df
Source dataset
uspto-grants-2015_10
Patent number
US09163027B2

Reaction notes

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