3-Methoxybenzyl chloride → HCID 58863820, compound

HRID 1352897Notes

Reaction equation

HRID 1352897 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:15]=[C:14]([N:16]([CH3:18])[CH3:17])[N:13]=[C:12]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:11]=2)[CH:6]=[CH:7][CH:8]=1.CCN(C(C)C)C(C)C.Cl[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=1>O1CCOCC1>[CH3:43][O:42][C:38]1[CH:37]=[C:36]([CH:41]=[CH:40][CH:39]=1)[CH2:35][N:22]1[CH2:23][CH2:24][N:19]([C:12]2[N:11]=[C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:15]=[C:14]([N:16]([CH3:18])[CH3:17])[N:13]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 699943-Methoxybenzyl chlorideHCID 81531DiisopropylethylamineHCID 68563369HCID 68563369, compound

Product 1

HCID 58863820HCID 58863820, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N4-(3-methoxyphenyl)-N6,N6-dimethyl-2-(1-piperazinyl)-4,6-pyrimidinediamine (36 mg, 0.1 mmol), DIPEA (52 mg, 0.4 mmol), and 1-(chloromethyl)-3-methoxybenzene (20 mg, 0.13 mmol) in 5 mL of dioxane was stirred at 100° C. for 16 h. The crude product was concentrated in vacuo and treated with saturated NaHCO3 (50 mL) and extracted with CH2Cl2 (3×50 mL). The organic layer was washed with brine (2×100 mL), dried over Na2SO4, and concentrated in vacuo. The crude product was purified by chromatography on silica using hexane/EtOAc (1:3), giving the desired product (32 mg, 70%).

Workup

  1. concentrationThe crude product was concentrated in vacuo
  2. additiontreated with saturated NaHCO3 (50 mL)
  3. extractionextracted with CH2Cl2 (3×50 mL)
  4. washThe organic layer was washed with brine (2×100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by chromatography on silica

Sources & evidence

ORD record
ord-8c683ca2c4fe4af496993a115af270c4
Source dataset
uspto-grants-2007_05
Patent number
US07220775B2

Reaction notes

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