Diisopropylethylamine → HCID 57861319, compound

HRID 1803925Notes

Reaction equation

HRID 1803925 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][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]1.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][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]3)[CH:7]=[CH:6][N:5]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514454tert-Butyl (3S)-3-(aminomethyl)pyrrolidine-1-carboxylateHCID 590282434-chloro-N-(3-chlorophenyl)pyrimidin-2-amine

Product 1

HCID 57861319HCID 57861319, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-N-(3-chlorophenyl)pyrimidin-2-amine (500 mg, 2.08 mmol) and tert-butyl (3S)-3-(aminomethyl)pyrrolidine-1-carboxylate (625 mg, 3.12 mmol) in THF (10 mL) is added diisopropylethylamine (0.73 mL, 4.16 mmol). The reaction is heated at reflux for 18 hours and then cooled to room temperature. The crude reaction is partitioned between EtOAc and sat. NaHCO3. The organic layer is dried (MgSO4), concentrated in vacuo, and purified over silica (MeOH/CH2Cl2) to afford 356 mg (42% yield) of the desired compound: MS (ESI, pos. ion) m/z: 404 (M+1).

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux for 18 hours
  3. customThe crude reaction
  4. customis 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-7ae759e2bca64f0f86b217e3726f6dfe
Source dataset
uspto-grants-2013_01
Patent number
US08354407B2

Reaction notes

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