2,4-Dichloropyrimidine → HCID 86685254, compound

HRID 522902Notes

Reaction equation

HRID 522902 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([NH:15][CH3:16])=[O:14].C(N(C(C)C)C(C)C)C>CC(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([NH:15][CH3:16])=[O:14])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 6765263-Amino-N-methylbenzamide

Product 1

HCID 86685254HCID 86685254, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To 2,4-dichloropyrimidine (250.0 mg, 1.678 mmol) and 3-amino-N-methylbenzamide (252 mg, 1.678 mmol) in 2-propanol (8390 μL) in a disposable sealed tube at RT was added N-ethyl-N-isopropylpropan-2-amine (585 μL, 3.36 mmol). The resulting reaction mixture was heated at 60° C. for 22 h, then to 70° C. for 23 h, then 80° C. for 3 days, cooled to RT, concentrated, purified using MPLC (5 g cartridge, 12 g column, 0 to 60% 90/10 CH2Cl2-MeOH in CH2Cl2) giving 3-(2-chloropyrimidin-4-ylamino)-N-methylbenzamide (389.0 mg).

Workup

  1. customThe resulting reaction mixture
  2. wait80° C. for 3 days
  3. temperaturecooled to RT
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-6c87dc1938ea44b1817703c266cdff67
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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