4-Methoxybenzylamine → N-(4-Methoxybenzyl)-4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxamide

HRID 1783557Notes

Reaction equation

HRID 1783557 reaction equation
[CH:1]([NH:4][C:5]1[C:10]([C:11](Cl)=[O:12])=[CH:9][N:8]=[C:7]([S:14][CH3:15])[N:6]=1)([CH3:3])[CH3:2].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1>O1CCCC1.ClCCl>[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:23][C:11]([C:10]2[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:6][C:7]([S:14][CH3:15])=[N:8][CH:9]=2)=[O:12])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 754524-MethoxybenzylamineHCID 539636504-(Isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic acid chloride

Product 1

HCID 54200478N-(4-Methoxybenzyl)-4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxamideYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. suspension of 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic acid chloride (as prepared in the above example, Preparation 16) in 30 mL of tetrahydrofuran is added 6.0 mL (46.3 mmol) of 4-methoxybenzylamine and 30 mL of tetrahydrofuran. The reaction suspension is allowed to warm briefly to room temperature, then stored at 0° C. overnight. The reaction mixture is diluted with dichloromethane, washed with 1N HCl and water. The combined aqueous phase is washed with dichloromethane. The combined organic phase is washed with a saturated solution of sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated. The residue is crystallized from ethyl acetate/hexane to give 3.27 g (61%) of the title compound: mp 176-177° C.

Workup

  1. washwashed with 1N HCl and water
  2. washThe combined aqueous phase is washed with dichloromethane
  3. washThe combined organic phase is washed with a saturated solution of sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-07636a58e7fc418da226ad5ecd156cb1
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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