Dichloromethane → HCID 178462661, compound

HRID 577205Notes

Reaction equation

HRID 577205 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH3:16])[CH2:11][CH2:10]2)=[N:7][CH:8]=1.[CH3:17][C:18]1[N:23]=[C:22]([SH:24])[N:21]=[C:20]([OH:25])[CH:19]=1.C(N(CC)CC)C.ClCCl>C(O)C>[CH2:15]([N:12]1[CH2:13][CH2:14][N:9]([C:6]2[N:7]=[CH:8][C:3]([CH2:2][S:24][C:22]3[N:21]=[C:20]([OH:25])[CH:19]=[C:18]([CH3:17])[N:23]=3)=[CH:4][CH:5]=2)[CH2:10][CH2:11]1)[CH3:16]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 59589454HCID 59589454, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178462661HCID 178462661, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1-[5-(bromomethyl)pyridin-2-yl]-4-ethylpiperazine (3.85 g, 13.54 mmol) and 6-methyl-2-sulfanylpyrimidin-4-ol (1.25 g, 8.86 mmol) in anhydrous ethanol at 0° C. was added triethylamine (5.47 g, 54.18 mmol). The reaction mixture was stirred overnight at room temperature. The solvent was evaporated, and the residue was purified by column chromatography using 0-15% methanol:dichloromethane to provide (2-({[6-(4-ethylpiperazin-1-yl)pyridin-3-yl]methyl}sulfanyl)-6-methylpyrimidin-4-ol as a white solid (1.82 g, 39% yield); 1H NMR (400 MHz, DMSO-d6): δ 0.99 (t, 3H), 2.18 (s, 3H), 2.31 (q, 2H), 2.56 (m, 4H), 3.42 (m, 4H), 4.23 (s, 2H), 6.01 (bs, 1H), 6.78 (d, J=8.8 Hz, 1H), 7.58 (d, J=8.8 Hz, 1H), 8.14 (s, 1H); LRMS (ES+) m/z 345.6.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ccdc2da779d34764a1dabb464d8e46cf
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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