Diisopropylethylamine → HCID 57861318, compound

HRID 1803922Notes

Reaction equation

HRID 1803922 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[N:3]=1.[NH2:16][CH2:17][C@@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C(N(C(C)C)CC)(C)C>C1COCC1>[Cl:15][C:11]1[CH:10]=[C:9]([NH:8][C:4]2[N:3]=[C:2]([NH:16][CH2:17][C@@H:18]3[CH2:22][CH2:21][CH2:20][N:19]3[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:7]=[CH:6][N:5]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 590282434-chloro-N-(3-chlorophenyl)pyrimidin-2-amine

Product 1

HCID 57861318HCID 57861318, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-N-(3-chlorophenyl)pyrimidin-2-amine, 3, (300 mg, 1.25 mmol) and tert-butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylate (500 mg, 2.50 mmol) in THF (10 mL) is added diisopropylethylamine (0.43 mL, 2.50 mmol). The reaction was heated at reflux for 18 hours and then cooled to room temperature. The crude reaction is then partitioned between EtOAc and sat. NaHCO3. The organic layer is dried (MgSO4), concentrated in vacuo, and purified over silica (MeOH/CH2Cl2) to afford 160 mg (32% yield) of the desired product: MS (ESI, pos. ion) m/z: 404 (M+1).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 hours
  3. customThe crude reaction
  4. customis then partitioned between EtOAc and sat. NaHCO3
  5. dry with materialThe organic layer is dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. custompurified over silica (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-919ebf20f3ae4f75a7e8ab30a4978ffe
Source dataset
uspto-grants-2013_01
Patent number
US08354407B2

Reaction notes

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