Diisopropylethylamine → 2-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide

HRID 1947826Notes

Reaction equation

HRID 1947826 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([NH:15][CH3:16])=[O:14].CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([NH:15][CH3:16])=[O:14])[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 3080722-Amino-N-methylbenzamide

Product 1

HCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamideYield 26.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,4,5-trichloropyrimidine (1.0 g, 5.4 mmol) and 2-amino-N-methylbenzamide (0.98 g, 6.5 mmol) in THF (5.0 mL) was charged with DIPEA (1.42 mL, 8.18 mmol) and the mixture allowed to stir at rt for 16 h. The reaction was quenched with NaHCO3 (10 mL) and extracted with EtOAc (15 mL). The organic layer was washed with brine (10 mL), dried over NaSO4, filtered, and concentrated in vacuo to yield a yellow solid which was recrystallized from EtOAc to afford 422 mg of 2-[(2,5-dichloropyrimidin-4-yl)amino]-N-methylbenzamide (yield: 26% yield*). Further material could be recovered from the mother liquors if desired.

Workup

  1. customThe reaction was quenched with NaHCO3 (10 mL)
  2. extractionextracted with EtOAc (15 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over NaSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a yellow solid which
  8. customwas recrystallized from EtOAc

Sources & evidence

ORD record
ord-951ee7f5585f40c28b479a88c99bbf2d
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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