Triethylamine → HCID 178429522, compound

HRID 577200Notes

Reaction equation

HRID 577200 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[N:24]=[CH:23][CH:22]=[CH:21][N:20]=1>C(O)C>[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:18][C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:5]=[C:4]([OH:9])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 220327572-(Bromomethyl)pyrimidineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429522HCID 178429522, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (867 mg, 6.1 mmol) was dissolved in absolute ethanol (130 mL), and then triethylamine (3.75 mL, 27.3 mmol) and 2-(bromomethyl)pyrimidine (1.57 g, 9.1 mmol) were added. The mixture was stirred overnight at room temperature. The solid was removed by filtration, and the filtrate was evaporated. The residue was triturated in water, filtered, and washed with water followed with diethyl ether. The solid was then dissolved in DCM and purified on silica gel using 10% DCM/MeOH to afford 6-methyl-2-[(pyrimidin-2-ylmethyl)sulfanyl]pyrimidin-4-ol (326 mg, 23% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.13 (s, 3H), 4.67 (s, 2H), 6.02 (bs, 1H), 7.42 (t, J=4.9 Hz, 1H), 8.78 (d, J=4.9 Hz, 2H); LRMS (ES+) m/z 235 (100%, M+1).

Workup

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

Sources & evidence

ORD record
ord-39b2f849e6764bc7bc0ff35f4242e311
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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