Dimethylformamide → 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-prop-2-ynyl-benzamide

HRID 1041404Notes

Reaction equation

HRID 1041404 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][C:8]#[CH:9])=[O:5].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[Cl:25][C:26]1[N:31]=[C:30](Cl)[C:29]([Cl:33])=[CH:28][N:27]=1>>[Cl:25][C:26]1[N:31]=[C:30]([NH:1][C:2]2[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=2[C:4]([NH:6][CH2:7][C:8]#[CH:9])=[O:5])[C:29]([Cl:33])=[CH:28][N:27]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 27644242-Amino-N-(prop-2-yn-1-yl)benzamide

Product 1

HCID 866340252-(2,5-dichloro-pyrimidin-4-ylamino)-N-prop-2-ynyl-benzamideYield 4%

Procedure

2-Amino-N-prop-2-ynyl-benzamide (4.20 g, 24.1 mmol) was dissolved in N,N-dimethylformamide (100 mL, 1.290 mol) and potassium carbonate (5.00 g, 36.2 mmol) was added. 2,4,5-Trichloro-pyrimidine (3.32 mL, 28.9 mmol) was added and the reaction was stirred for 48 hours. The reaction was concentrated under reduced pressure and the residue was taken up in DCM (300 mL) and washed with water (300 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography using a gradient of 0-50% EtOAc/hex as the eluting solvent to obtain 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-prop-2-ynyl-benzamide as a pale yellow solid (298 mg, 4%). m.p.=188-191° C.; LCMS (m/e) 321 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 11.53 (s, 1H), 8.76 (d, 1H, J=8.5 Hz), 8.25 (s, 1H), 7.66-7.53 (m, 2H), 7.23-7.14 (m, 1H), 6.39 (bs, 1H), 4.34-4.25 (m, 2H), 2.34 (t, 1H, J=2.5 Hz).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. washwashed with water (300 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-cfde8d8962e64d438411bf93a095cf52
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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