Diethyl Ether → HCID 178423372, compound

HRID 577199Notes

Reaction equation

HRID 577199 reaction equation
Br[CH2:2][C:3]1[N:7]2[CH:8]=[CH:9][C:10](C)=[CH:11][C:6]2=[N:5][CH:4]=1.[CH3:13][C:14]1[N:19]=[C:18]([SH:20])[N:17]=[C:16]([OH:21])[CH:15]=1.[CH2:22](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[N:7]3[CH:8]=[C:9]([CH3:22])[CH:10]=[CH:11][C:6]3=[N:5][CH:4]=2)[N:17]=[C:16]([OH:21])[CH:15]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 59589487HCID 59589487, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178423372HCID 178423372, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(bromomethyl)-7-methylimidazo[1,2-a]pyridine (1.0 g, 4.44 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (0.407 g, 2.88 mmol) in anhydrous ethanol (50 mL) at 0° C. was added triethylamine (0.898 g, 8.88 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-[({6-methylimidazo[1,2-a]pyridin-3-yl}methyl)sulfanyl]pyrimidin-4-ol as a white solid (826 mg, 65% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.25 (s, 3H), 2.31 (s, 3H), 4.79 (s, 2H), 6.04 (bs, 1H), 7.15 (d, J=8.0 Hz, 1H), 7.51 (d, J=8.0 Hz, 1H), 7.54 (s, 1H), 8.32 (s, 1H); M+ 286.5.

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-24a07b48e70a4fc1a019a4c6cace885e
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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