Ethyl 2-aminobenzoate → HCID 21236519, compound

HRID 1864066Notes

Reaction equation

HRID 1864066 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH3:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(N(C(C)C)CC)(C)C>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][C:11]2[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([CH3:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6877Ethyl 2-aminobenzoateHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 81531Diisopropylethylamine

Product 1

HCID 21236519HCID 21236519, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

2,4-Dichloro-5-methylpyrimidine (28.1 g, 4172 mmol), ethyl 2-aminobenzoate (26.7 mL, 181 mmol), diisopropylethylamine (33 mL, 190 mmol) and ethanol (200 mL) were mixed together then equally divided and placed in two 350 mL pressure vessels. They were then capped and heated to 130° C. for three days. Upon cooling to room temperature, the precipitated product was collected and washed with ethanol followed by hexanes and then dried to give 4.5 g (9%) of ethyl 2-[(2-chloro-5-methyl-4-pyrimidinyl)amino]benzoate as an off-white solid. MS: M(C14H14ClN3O2)=291.7, (M+H)+=292.2 and 294.2.

Workup

  1. customThey were then capped
  2. temperatureUpon cooling to room temperature
  3. customthe precipitated product was collected
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-0c17ca5cb638495ea451d405e4aa48d3
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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