Triethylamine → HCID 62481336, compound

HRID 2175403Notes

Reaction equation

HRID 2175403 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=1.C(N(CC)CC)C.[CH3:17][N:18]1[CH:22]=[C:21]([CH2:23][NH2:24])[CH:20]=[N:19]1>O1CCOCC1.C(OCC)(=O)C>[Cl:8][C:6]1[N:5]=[C:4]([CH3:9])[N:3]=[C:2]([NH:24][CH2:23][C:21]2[CH:20]=[N:19][N:18]([CH3:17])[CH:22]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2349974,6-Dichloro-2-methylpyrimidineHCID 671225(1-methyl-1H-pyrazol-4-yl)methanamine

Product 1

HCID 62481336HCID 62481336, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 4,6-dichloro-2-methylpyrimidine (100 mg, 0.61 mmol) in dioxane (1 mL) was added triethylamine (0.3 mL, 2.15 mmol) and (1-methyl-1H-pyrazol-4-yl)methanamine (68 mg, 0.61 mmol). The resulting mixture was microwave irradiated at 150° C. for 30 minutes. The reaction was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase was concentrated and flash column separation using a 10-100% ethyl acetate/hexane gradient gave 1-1 as a white solid (121 mg, 83%). MS (M+H)+: observed=238.0857, calculated=238.0854.

Workup

  1. customThe resulting mixture was microwave irradiated at 150° C. for 30 minutes
  2. washwashed with saturated sodium bicarbonate solution
  3. concentrationThe organic phase was concentrated
  4. customflash column separation

Sources & evidence

ORD record
ord-84636a53f2c34fec941cb87ad14382fb
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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