Triethylamine → HCID 178438087, compound

HRID 630254Notes

Reaction equation

HRID 630254 reaction equation
Br[CH2:2][C:3]1[C:4]([CH2:10][CH3:11])=[N:5][O:6][C:7]=1[CH2:8][CH3:9].[CH3:12][C:13]1[N:18]=[C:17]([SH:19])[N:16]=[C:15]([OH:20])[CH:14]=1.C(N(CC)CC)C>C(O)C>[CH2:10]([C:4]1[C:3]([CH2:2][S:19][C:17]2[N:16]=[C:15]([OH:20])[CH:14]=[C:13]([CH3:12])[N:18]=2)=[C:7]([CH2:8][CH3:9])[O:6][N:5]=1)[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59589374HCID 59589374, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178438087HCID 178438087, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(bromomethyl)-3,5-diethyl-1,2-oxazole (4.6 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (440 mg, 3.3 mmol), and triethylamine (1.3 mL, 9.3 mmol) in absolute ethanol (35 mL) was stirred at room temperature overnight. The mixture was evaporated. The residue was treated with water (50 mL). The solid material was removed by filtration. The solid was washed with diethyl ether (3×25 mL). The filtrate was recovered, extracted with water (2×75 mL), dried over MgSO4, filtered, evaporated, and dried in vacuo, affording the title compound (220 mg, 30% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.18 (m, 6H), 2.21 (s, 3H), 2.65 (m, 2H), 2.83 (m, 2H), 4.22 (s, 2H), 6.02 (s, 1H); M+280.

Workup

  1. customThe mixture was evaporated
  2. additionThe residue was treated with water (50 mL)
  3. customThe solid material was removed by filtration
  4. washThe solid was washed with diethyl ether (3×25 mL)
  5. customThe filtrate was recovered
  6. extractionextracted with water (2×75 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customdried in vacuo

Sources & evidence

ORD record
ord-a458c9826a28473fb4f0fbe4a17eed5b
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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