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

HRID 511257Notes

Reaction equation

HRID 511257 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. 1H NMR (CD3OD, 400 MHz): δ=2.93 (s, 3 H), 7.21 (td, J=7.64, 1.14 Hz, 1 H), 7.56 (ddd, J=8.53, 7.26, 1.64 Hz, 1 H), 7.71 (dd, J=7.83, 1.26 Hz, 1 H), 8.30 (s, 1 H) 8.63 (dd, J=8.59, 0.76 Hz, 1 H). MS (ES+): m/z 296.90 [MH+] (ZQ3, polar—5 min).

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-24f1308c86d742129201dccfe25f02ab
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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