3,4-Dichloroaniline → HCID 86679758, compound

HRID 77469Notes

Reaction equation

HRID 77469 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].Cl[C:11]1[CH:16]=[C:15]([CH2:17][O:18][CH3:19])[N:14]=[CH:13][N:12]=1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:11]2[CH:16]=[C:15]([CH2:17][O:18][CH3:19])[N:14]=[CH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 143061714-Chloro-6-(methoxymethyl)pyrimidine

Product 1

HCID 86679758HCID 86679758, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3,4-dichloroaniline (1.328 g, 8.20 mmol) and 4-chloro-6-(methoxymethyl)pyrimidine (0.65 g, 4.10 mmol) in dioxane (20.5 ml) was heated at 100° C. for 54 h, cooled to room temperature and concentrated onto Na2SO4. The residue was purified on silica gel using 50-100% ethyl acetate in hexanes, then 10-15% methanol in ethyl acetate. The desired fractions were concentrated to give a dark brown solid which was triturated with DCM to yield N-(3,4-dichlorophenyl)-6-(methoxymethyl)pyrimidin-4-amine as a brown solid (0.66 g, 57%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.67 (1H, d, J=1.00 Hz), 7.69 (1H, d, J=2.51 Hz), 7.44 (1H, d, J=8.53 Hz), 7.29 (1H, dd, J=8.53, 2.51 Hz), 6.95 (1H, br. s.), 6.81 (1H, d, J=1.00 Hz), 4.45 (1H, d, J=0.50 Hz), 3.50 (2H, s). LCMS: R.T.=0.77; [M+H]+=283.98.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated onto Na2SO4
  3. customThe residue was purified on silica gel using 50-100% ethyl acetate in hexanes
  4. concentrationThe desired fractions were concentrated
  5. customto give a dark brown solid which
  6. customwas triturated with DCM

Sources & evidence

ORD record
ord-b8a0ca2371a44ad59da3fa68535a8674
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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