Diethyl Ether → HCID 178429428, compound

HRID 577198Notes

Reaction equation

HRID 577198 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]([CH3:10])[N:8]=[N:9][C:5]=2[CH:4]=1.[CH3:13][C:14]1[N:19]=[C:18]([SH:20])[N:17]=[C:16]([OH:21])[CH:15]=1.C(N(CC)CC)C.CCOCC>C(O)C.ClCCl>[CH3:13][C:14]1[N:19]=[C:18]([S:20][CH2:2][C:3]2[CH:12]=[CH:11][C:6]3[N:7]([CH3:10])[N:8]=[N:9][C:5]=3[CH:4]=2)[N:17]=[C:16]([OH:21])[CH:15]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 27954185-(Bromomethyl)-1-methyl-1H-benzotriazoleHCID 178429541HCID 178429541, compound

Product 1

HCID 178429428HCID 178429428, compoundYield 115.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-(bromomethyl)-1-methyl-1H-1,2,3-benzotriazole (1.0 g, 4.22 mmol) and 6-methyl-2-sulfanylpyrimidin-4-ol (0.404 g, 2.87 mmol) in anhydrous ethanol (50 mL) at 0° C. was added triethylamine (0.894 g, 8.84 mmol). Then, the reaction mixture was allowed to stir at room temperature overnight. The solvent was evaporated to provide a crude residue. Ether was added to precipitate the triethylamine hydrochloride salt. The solid was filtered and washed with ether several times. The solvent was evaporated to provide a crude residue, which was purified by Combiflash using 0-10% methanol:dichloromethane to provide 6-methyl-2-{[(1-methyl-1H-1,2,3-benzotriazol-5-yl)methyl]sulfanyl}pyrimidin-4-ol as a white solid (953 mg, 75% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.21 (s, 3H), 4.28 (s, 2H), 4.55 (s, 3H), 6.04 (bs, 1H), 7.62 (d, J=8.7 Hz, 1H), 7.80 (d, J=8.7 Hz, 1H), 8.07 (s, 1H); M+ 287.5.

Workup

  1. customThe solvent was evaporated
  2. customto provide a crude residue
  3. customto precipitate the triethylamine hydrochloride salt
  4. filtrationThe solid was filtered
  5. washwashed with ether several times
  6. customThe solvent was evaporated
  7. customto provide a crude residue, which
  8. customwas purified by Combiflash

Sources & evidence

ORD record
ord-f8c7efb80e784e4898f3dcf66612574f
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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