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

HRID 219703Notes

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[CH2:20][CH2:19][CH2:18]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:22][CH2:23][CH2:24][O:25][C:26](=[O:28])[CH3:27].C(N(CC)CC)C>CN(C)C=O>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:12][CH2:13][N:14]([CH2:22][CH2:23][CH2:24][O:25][C:26](=[O:28])[CH3:27])[CH2:15][CH2:16]2)[CH:8]=[C:7]([CH:17]2[CH2:20][CH2:19][CH2:18]2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

5.5 g of 2-tert-butyl-4-piperazin-1-yl-6-cyclobutyl-pyrimidine (20.0 mmol), 3.15 g of acetic acid 3-chloro-propyl ester (23.1 mmol) and 2.76 g of triethylamine (27.3 mmol) were dissolved in 70 ml of dimethylformamide and stirred for 12 h at 80° C. After cooling, the dimethylformamide was evaporated, and 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 (7 g) was directly used in the subsequent reaction step.

Workup

temperatureAfter cooling
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 (7 g) was directly used in the subsequent reaction step

Sources & evidence

ORD record: ord-9f63be50d3af44f18c736260120ee1a6
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202868B2

Reaction notes

Loading…