Sodium Iodide → Acetic acid 3-[4-(2-tert-butyl-6-cyclopropyl-pyrimidin-4-yl)-piperazin-1-yl]-propyl ester

HRID 219711Notes

Reaction equation

[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:17]2[CH2:19][CH2:18]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:21][CH2:22][CH2:23][O:24][C:25](=[O:27])[CH3:26].C(N(CC)CC)C.[I-].[Na+]>CN(C)C=O>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:12][CH2:13][N:14]([CH2:21][CH2:22][CH2:23][O:24][C:25](=[O:27])[CH3:26])[CH2:15][CH2:16]2)[CH:8]=[C:7]([CH:17]2[CH2:19][CH2:18]2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

2.9 g of 2-tert-Butyl-4-piperazin-1-yl-6-cyclopropyl-pyrimidine (11.1 mmol), 1.8 g acetic acid 3-chloro-propyl ester (13.2 mmol), 1.38 g of triethylamine (13.7 mmol), and a spatula tip of sodium iodide were dissolved in 50 ml of dimethylformamide and stirred for 8 h at 80° C. After cooling to room temperature, the dimethylformamide was evaporated. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated. The crude product (3.7 g) was directly used in the subsequent reaction step.

Workup

temperatureAfter cooling to room temperature
customthe dimethylformamide was evaporated
customThe reaction mixture was partitioned between water and ethyl acetate
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
customthe solvent was evaporated
customThe crude product (3.7 g) was directly used in the subsequent reaction step

Sources & evidence

ORD record: ord-184b0733e8444260864a6e980e6ad5c3
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202868B2

Reaction notes

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