Potassium Carbonate → HCID 86633872, compound

HRID 1040804Notes

Reaction equation

HRID 1040804 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].C(N(C(C)C)CC)(C)C.[Cl:28][C:29]1[N:34]=[C:33](Cl)[C:32]([Cl:36])=[CH:31][N:30]=1>CN(C=O)C.CN1C(=O)CCC1>[Cl:28][C:29]1[N:34]=[C:33]([NH:1][C:2]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=2[C:4]([NH:6][CH3:7])=[O:5])[C:32]([Cl:36])=[CH:31][N:30]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 1871970634810-84-9

Product 1

HCID 86633872HCID 86633872, compoundYield 138.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-Amino-5,N-dimethyl-benzamide (2.0 g, 12.2 mmol), potassium carbonate (2 eq) or diisopropylethylamine (2 eq) and 2,4,5-trichloropyrimidine (2.24 g, 12.2 mmol) were combined in DMF or NMP (25 mL) and heated at 50-100° C. until HPLC indicated consumption of the starting materials. The reaction can either be concentrated in vacuo or directly partitioned between water and dichloromethane. The product is extracted, dried and concentrated to afford the crude material, which is then chromatographed on silica gel (ethyl acetate:hexanes) to afford 2-(2,5-dichloro-pyrimidin-4-ylamino)-5,N-dimethyl-benzamide (5.25 g, 56%) as a light yellow solid. m.p.=192-210° C.; LCMS (m/e) 311 (M+1); 1H-NMR (DMSO-d6, 400 MHz) δ 12.02 (s, 1H), 8.82 (m, 1H), 8.45 (s, 1H), 8.38 (d, 1H, J=8.5 Hz), 7.63 (s, 1H), 7.42 (d, 1H, J=8.5 Hz), 2.80 (d, 3H, J=4.4 Hz), 2.34 (s, 3H).

Workup

  1. customconsumption of the starting materials
  2. customThe reaction
  3. concentrationcan either be concentrated in vacuo
  4. customdirectly partitioned between water and dichloromethane
  5. extractionThe product is extracted
  6. customdried
  7. concentrationconcentrated
  8. customto afford the crude material, which
  9. customis then chromatographed on silica gel (ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-48e1a09d7c1e4c108d3837d8e0548085
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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