Triethylamine → 5-(chloromethyl)-N-(4-chlorophenyl)pyrimidin-2-amine

HRID 77451Notes

Reaction equation

HRID 77451 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][N:10]=2)=[CH:4][CH:3]=1.CCN(CC)CC.CS([Cl:28])(=O)=O>C(Cl)Cl>[Cl:28][CH2:15][C:12]1[CH:11]=[N:10][C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86679732(2-(4-Chlorophenylamino)pyrimidin-5-yl)methanol

Product 1

HCID 866797335-(chloromethyl)-N-(4-chlorophenyl)pyrimidin-2-amineYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of (2-(4-chlorophenylamino)pyrimidin-5-yl)methanol (0.15 g, 0.636 mmol) and Et3N (0.177 ml, 1.273 mmol) in DCM (6.4 mL) was cooled to 0° C. and methanesulfonyl chloride (0.099 mL, 1.273 mmol) was added. The reaction was stirred for 1.5 h while warming to room temperature. The mixture was diluted with DCM and quenched with sat. NaHCO3. The organic layer was isolated and dried over Na2SO4, then concentrated to give crude 5-(chloromethyl)-N-(4-chlorophenyl)pyrimidin-2-amine as a yellow solid (0.1 g, 62%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.46 (2H, s), 7.58 (2H, d, J=8.78 Hz), 7.31 (2H, d, J=8.78 Hz), 7.25 (1H, br. s.), 4.53 (2H, s).

Workup

  1. temperaturewhile warming to room temperature
  2. customquenched with sat. NaHCO3
  3. customThe organic layer was isolated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-31353fc5599446a8a0da96cd8fcbb31f
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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