Potassium Carbonate → HCID 86633872, compound

HRID 1687112Notes

Reaction equation

HRID 1687112 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-5a7ea3fe311347e3af62a12c8d0a124b
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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