Triethylamine → HCID 178429510, compound

HRID 577207Notes

Reaction equation

HRID 577207 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.C(N(CC)CC)C.Br[CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[N:23][CH:24]=1>C(O)C>[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[N:23][CH:24]=2)[N:5]=[C:4]([OH:9])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 144349195-(Bromomethyl)pyrimidineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429510HCID 178429510, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (483 mg, 3.4 mmol) was dissolved in absolute ethanol (70 mL), and triethylamine (1.4 mL, 10.2 mmol) and 5-(bromomethyl)pyrimidine (882 mg, 5.1 mmol) were added. The mixture was stirred overnight at room temperature. The solid was filtered. The filtrate was evaporated. The residue was triturated in water, filtered, and washed with water followed with diethyl ether. The solid was dissolved in DCM and purified on silica gel using 10% DCM/MeOH to afford 6-methyl-2-[(pyrimidin-5-ylmethyl)sulfanyl]pyrimidin-4-ol (12 mg, 2% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.19 (s, 3H), 4.34 (s, 2H), 6.02 (bs, 1H), 8.88 (s, 2H), 9.05 (s, 1H); LRMS (ES) m/z 235 (100%, M+1).

Workup

  1. filtrationThe solid was filtered
  2. customThe filtrate was evaporated
  3. customThe residue was triturated in water
  4. filtrationfiltered
  5. washwashed with water
  6. dissolutionThe solid was dissolved in DCM
  7. custompurified on silica gel using 10% DCM/MeOH

Sources & evidence

ORD record
ord-981566e4182b40fbb988bd939f4848be
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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