Triethylamine → HCID 178429519, compound

HRID 576994

Reaction equation

HRID 576994 reaction equation
Br.Br[CH2:3][C:4]1[N:8]([CH3:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]=1.[CH3:14][C:15]1[N:20]=[C:19]([SH:21])[N:18]=[C:17]([OH:22])[CH:16]=1.C(N(CC)CC)C>C(O)C>[CH3:14][C:15]1[N:20]=[C:19]([S:21][CH2:3][C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=3[N:5]=2)[N:18]=[C:17]([OH:22])[CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 242294512-(Bromomethyl)-1-methyl-1H-benzimidazole hydrobromideHCID 178429541HCID 178429541, compound

Product 1

HCID 178429519HCID 178429519, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(bromomethyl)-1-methyl-benzimidazole hydrobromide (6.8 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (740 mg, 5.2 mmol), and triethylamine (4 mL, 28.7 mmol) in absolute ethanol (30 mL) was stirred at room temperature overnight. The mixture was recovered, evaporated, and then co-evaporated with EtOAc (20 mL). The solid residue was treated with water (200 mL). The solid product was recovered by filtration, washed with water (2×20 mL), diethyl ether (2×20 mL), and hexanes (2×20 mL), and then dried in vacuo, affording 6-methyl-2-{[(1-methyl-1H-benzimidazol-2-yl)methyl]sulfanyl}pyrimidin-4-ol (1.3 g, 90% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.18 (s, 3H), 3.83 (s, 3H), 4.70 (s, 2H), 6.02 (s, 1H), 7.19 (m, 2H), 7.53 (m, 2H); M+ 287. The product was used without further purification.

Workup

  1. customThe mixture was recovered
  2. customevaporated
  3. additionThe solid residue was treated with water (200 mL)
  4. filtrationThe solid product was recovered by filtration
  5. washwashed with water (2×20 mL), diethyl ether (2×20 mL), and hexanes (2×20 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d81ca144a97f4585b75f90a410418912
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Linked notes

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