Triethylamine → HCID 178429528, compound

HRID 577186Notes

Reaction equation

HRID 577186 reaction equation
Br[CH2:2][C:3]1[C:7]([Cl:8])=[CH:6][N:5]([CH3:9])[N:4]=1.[CH3:10][C:11]1[N:16]=[C:15]([SH:17])[N:14]=[C:13]([OH:18])[CH:12]=1.C(N(CC)CC)C>C(O)C>[Cl:8][C:7]1[C:3]([CH2:2][S:17][C:15]2[N:14]=[C:13]([OH:18])[CH:12]=[C:11]([CH3:10])[N:16]=2)=[N:4][N:5]([CH3:9])[CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 595893993-(bromomethyl)-4-chloro-1-methyl-1H-pyrazoleHCID 178429541HCID 178429541, compound

Product 1

HCID 178429528HCID 178429528, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(bromomethyl)-4-chloro-1-methyl-1H-pyrazole (61.7 mmol) in absolute ethanol (250 mL) was added 6-methyl-2-sulfanylpyrimidin-4-ol (5.84 g, 41.1 mmol) and triethylamine (23.0 mL, 165 mmol) at 0° C. The mixture was stirred at room temperature overnight. The white solid was filtered and washed with diethyl ether (300-500 mL). The filtrate was recovered, and the solvent was evaporated. The residue triturated in water, filtered, and washed with water (3×300 mL) and then DCM (50 mL). The solid was died under vacuum overnight. 2-{[(4-chloro-1-methyl-1H-pyrazol-3-yl)methyl)sulfanyl}-6-methylpyrimidin-4-ol was obtained as a white solid (5.48 g, 49% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 2.20 (bs, 3H), 3.78 (s, 3H), 4.35 (s, 2H), 6.05 (bs, 1H), 7.92 (s, 1H); LRMS (ES+) m/z 271 (100%, M+1); 273 (35%, M+3).

Workup

  1. filtrationThe white solid was filtered
  2. washwashed with diethyl ether (300-500 mL)
  3. customThe filtrate was recovered
  4. customthe solvent was evaporated
  5. customThe residue triturated in water
  6. filtrationfiltered
  7. washwashed with water (3×300 mL)
  8. customwas died under vacuum overnight

Sources & evidence

ORD record
ord-424308afa3374b7ca4a9edfa18390111
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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