Diethyl Ether → HCID 178437123, compound

HRID 630151Notes

Reaction equation

HRID 630151 reaction equation
Br[CH2:2][C:3]1[C:8]([CH2:9][CH3:10])=[CH:7][N:6]=[CH:5][C:4]=1[CH2:11][CH3:12].[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>[CH2:11]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH2:9][CH3:10])[C:3]=1[CH2:2][S:20][C:18]1[N:17]=[C:16]([OH:21])[CH:15]=[C:14]([CH3:13])[N:19]=1)[CH3:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 595893084-(Bromomethyl)-3,5-diethylpyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178437123HCID 178437123, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of crude 4-(bromomethyl)-3,5-diethylpyridine (2.07 g, 9.07 mmol) and 6-methyl-2-sulfanylpyrimidin-4-ol (0.838 g, 5.89 mmol) in anhydrous ethanol (50 mL) at 0° C. was added triethylamine (3.21 g, 4.42 mL 31.75 mmol), and 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 hydrobromide salt. The solid was filtered and washed with ether several times. The combined ether layers were evaporated, and the crude residue was purified by Combiflash using 0-10% MeOH in dichloromethane to provide 2-{[(3,5-diethylpyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol as a white solid; 1H NMR (400 MHz, DMSO-d6): δ 1.23 (t, 6H), 1.40 (t, 3H), 2.64 (q, 4H), 4.44 (q, 2H), 8.36 (s, 2H); M+1 290.4.

Workup

  1. customThe solvent was evaporated
  2. customto provide a crude residue
  3. customto precipitate the triethylamine hydrobromide salt
  4. filtrationThe solid was filtered
  5. washwashed with ether several times
  6. customThe combined ether layers were evaporated
  7. customthe crude residue was purified by Combiflash

Sources & evidence

ORD record
ord-345715652de54e72a8dd39c99ddcd2a0
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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