Ethanol → 4-(1-Bromo-2,2-diethoxy-ethyl)-2-methylsulfanyl-pyrimidine

HRID 1355546Notes

Reaction equation

HRID 1355546 reaction equation
[CH2:1]([O:3][CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([S:12][CH3:13])[N:7]=1)[CH3:2].C1C(=O)N([Br:21])C(=O)C1.[CH3:22][CH2:23][OH:24]>>[Br:21][CH:5]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]([S:12][CH3:13])[N:7]=1)[CH:4]([O:24][CH2:23][CH3:22])[O:3][CH2:1][CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 67184N-bromobutanimideHCID 673279474-(2-Ethoxy-vinyl)-2-methylsulfanyl-pyrimidine

Product 1

HCID 185069174-(1-Bromo-2,2-diethoxy-ethyl)-2-methylsulfanyl-pyrimidine

Conditions

Temperature
0 °C

Procedure

4-(2-Ethoxy-vinyl)-2-methylsulfanyl-pyrimidine (18-2, 0.236 g, 1.20 mmol) was dissolved in 5 mL EtOH and the resulting solution was cooled to 0° C. NBS (0.214 g, 1.20 mmol) was added in small portions. After 2 h the reaction was concentrated in vacuo. Purification by flash column chromatography (eluting with 98:2 DCM/MeOH) provided the titled compound. 1H NMR (CDCl3) δ 8.50 (d, 1H, J=5.0 Hz), 7.09 (d, 1H, J=5.1 Hz), 5.05 (d, 1H, J=6.8 Hz), 4.81 (d, 1H, J=6.9 Hz), 3.77 (m, 2H), 3.53 (m, 2H), 2.57 (s, 3H), 1.26 (t, 3H, J=7.0 Hz), 1.08 t, 3H, J=7.1 Hz).

Workup

  1. concentrationAfter 2 h the reaction was concentrated in vacuo
  2. customPurification
  3. washby flash column chromatography (eluting with 98:2 DCM/MeOH)

Sources & evidence

ORD record
ord-f6d5c4d3b5c446d89e0e147657ae1cb3
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

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