Ammonia → (4-{-3-[4-(2-Amino-ethoxy)-3-ethyl-5-methyl-phenyl]-[1,2,4]oxadiazol-5-yl}-6-methyl-pyrimidin-2-yl)-diethyl-amine

HRID 2069458Notes

Reaction equation

[CH2:1]([N:3]([CH2:33][CH3:34])[C:4]1[N:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:28]=[C:27]([CH3:29])[C:18]([O:19][CH2:20][CH2:21]OS(C)(=O)=O)=[C:17]([CH2:30][CH3:31])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:32])[N:5]=1)[CH3:2].[NH3:35]>CO>[NH2:35][CH2:21][CH2:20][O:19][C:18]1[C:27]([CH3:29])=[CH:28][C:15]([C:12]2[N:11]=[C:10]([C:8]3[CH:7]=[C:6]([CH3:32])[N:5]=[C:4]([N:3]([CH2:33][CH3:34])[CH2:1][CH3:2])[N:9]=3)[O:14][N:13]=2)=[CH:16][C:17]=1[CH2:30][CH3:31]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methanesulfonic acid 2-{4-[5-(2-diethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-ethyl ester (850 mg, 1.74 mmol), derived from Example 102, in 7M NH3 in MeOH (20 mL) is stirred at 60° C. for 18 h. Volatiles are then evaporated and the residue is purified by CC (eluting with EA/MeOH 10:1) to give (4-{-3-[4-(2-amino-ethoxy)-3-ethyl-5-methyl-phenyl]-[1,2,4]oxadiazol-5-yl}-6-methyl-pyrimidin-2-yl)-diethyl-amine as a yellow solid (700 mg); LC-MS: tR=0.92 min; [M+H]+=410.95.

Workup

customVolatiles are then evaporated
customthe residue is purified by CC (eluting with EA/MeOH 10:1)

Sources & evidence

ORD record: ord-78f7accc388243a3b0a28484464d772a
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299086B2

Reaction notes

Loading…