S-Benzylthiuronium chloride → [2-Benzylsulfanyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-ylmethyl]-carbamic acid tert-butyl ester

HRID 1914511Notes

Reaction equation

HRID 1914511 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][C:9]#[C:10][C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:25]([S:32][C:33](=[NH:35])[NH2:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][C:9]1[CH:10]=[C:11]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[N:35]=[C:33]([S:32][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:34]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10852S-Benzylthiuronium chlorideHCID 11430Potassium CarbonateHCID 66832372[4-Oxo-4-(4-trifluoromethyl-phenyl)but-2-ynyl]-carbamic acid tert-butyl ester

Product 1

HCID 66832575[2-Benzylsulfanyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-ylmethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of [4-oxo-4-(4-trifluoromethyl-phenyl)but-2-ynyl]-carbamic acid tert-butyl ester (3.0 g, 9.17 mmol) and 2-benzyl-2-thiopseudo-urea hydrochloride (2.1 g, 10.1 mmol) in freshly distilled CH3CN (100 mL) was added K2CO3 (1.9 g, 13.8 mmol) at rt. After 12 h the resulting mixture was partitioned between H2O (75 mL) and DCM (50 mL). The layers were separated and the aqueous layer was extracted with DCM (2×50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The resulting solid was used without purification. MS (ESI): mass calcd. for C24H24F3N3O2S, 475.2; m/z found, 476.3 [M+H]+. 1H NMR (CDCl3) δ 8.15 (d, J=8.14 Hz, 2H), 7.75 (d, J=8.28 Hz, 2H), 7.51-7.47 (m, 2H), 7.39-7.31 (m, 4H), 5.52 (s, 1H), 4.51 (s, 2H), 4.43 (d, J=5.48 Hz, 2H), 1.51 (s, 9H).

Workup

  1. customAfter 12 h the resulting mixture was partitioned between H2O (75 mL) and DCM (50 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with DCM (2×50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting solid was used without purification

Sources & evidence

ORD record
ord-0e07ceee76aa4383b29e2311fe38afe0
Source dataset
uspto-grants-2013_12
Patent number
US08614201B2

Reaction notes

Loading…