Triethylamine → (S)-3-methyl-6-(4-pyrimidinyl)-2-(3-(4-(3-(pyrrolidin-1-yl)pyrrolidin-1-yl)phenyl)piperazin-1-yl)-pyrimidin-4-one

HRID 1784684Notes

Reaction equation

HRID 1784684 reaction equation
Cl.Cl.Cl.Cl.[N:5]1([C@H:10]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([C@H:21]4[CH2:26][NH:25][CH2:24][CH2:23][NH:22]4)=[CH:17][CH:16]=3)[CH2:11]2)[CH2:9][CH2:8][CH2:7][CH2:6]1.C(N(CC)CC)C.Cl[C:35]1[N:40]([CH3:41])[C:39](=[O:42])[CH:38]=[C:37]([C:43]2[CH:48]=[CH:47][N:46]=[CH:45][N:44]=2)[N:36]=1>O1CCCC1>[CH3:41][N:40]1[C:39](=[O:42])[CH:38]=[C:37]([C:43]2[CH:48]=[CH:47][N:46]=[CH:45][N:44]=2)[N:36]=[C:35]1[N:25]1[CH2:24][CH2:23][NH:22][C@@H:21]([C:18]2[CH:17]=[CH:16][C:15]([N:12]3[CH2:13][CH2:14][CH:10]([N:5]4[CH2:6][CH2:7][CH2:8][CH2:9]4)[CH2:11]3)=[CH:20][CH:19]=2)[CH2:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-oneHCID 67117390(S)-2-(4-((S)-3-(pyrrolidin-1-yl)pyrrolidin-1-yl)phenyl)piperazine tetrahydrochloride

Product 1

HCID 53628946(S)-3-methyl-6-(4-pyrimidinyl)-2-(3-(4-(3-(pyrrolidin-1-yl)pyrrolidin-1-yl)phenyl)piperazin-1-yl)-pyrimidin-4-oneYield 66.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (S)-2-(4-((S)-3-(pyrrolidin-1-yl)pyrrolidin-1-yl)phenyl) piperazine tetrahydrochloride (99 mg, 0.22 mmol) in tetrahydrofuran (5 mL) was added triethylamine (0.20 mL, 1.40 mmol) and 2-chloro-3-methyl-6-(4-pyrimidinyl)-3H-pyrimidin-4-one (45 mg, 0.20 mmol) at room temperature. After stirring for 24 h, the reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane and sodium bicarbonate aqueous solution, and the solution was passed through CHEM ELUT CE1010 (manufactured by VARIAN). The filtrate was concentrated, and the resulting crystals were washed in a mixture of diisopropyl ether and ethanol to afford (S)-3-methyl-6-(4-pyrimidinyl)-2-(3-(4-(3-(pyrrolidin-1-yl)pyrrolidin-1-yl)phenyl)piperazin-1-yl)-pyrimidin-4-one (65 mg, 66%) as a pale yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. concentrationThe filtrate was concentrated
  4. washthe resulting crystals were washed in a mixture of diisopropyl ether and ethanol

Sources & evidence

ORD record
ord-550edba2ff7943a2b0d596302e1f3a7e
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

Loading…