Methyl N-(triethylammoniosulfonyl)carbamate → {4-[2-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-6-methyl-pyrimidin-2-yl}-isopropyl-amine

HRID 2069472Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:31]([CH3:32])=[CH:30][C:12]([C:13]([NH:15][CH2:16][C:17]([C:19]2[CH:24]=[C:23]([CH3:25])[N:22]=[C:21]([NH:26][CH:27]([CH3:29])[CH3:28])[N:20]=2)=[O:18])=O)=[CH:11][C:10]=1[CH2:33][CH3:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH2:1]([O:8][C:9]1[C:31]([CH3:32])=[CH:30][C:12]([C:13]2[O:18][C:17]([C:19]3[CH:29]=[C:27]([CH3:28])[N:26]=[C:21]([NH:22][CH:23]([CH3:25])[CH3:24])[N:20]=3)=[CH:16][N:15]=2)=[CH:11][C:10]=1[CH2:33][CH3:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of crude 4-benzyloxy-3-ethyl-N-[2-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-2-oxo-ethyl]-5-methyl-benzamide (300 mg, 0.65 mmol) in THF (10 mL), Burgess reagent (775 mg, 3.3 mmol) is added. The mixture is stirred at 80° C. for 18 h before it is concentrated. The crude product is purified on prep. TLC plates with Heptane/EA 1:1 to give {4-[2-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-6-methyl-pyrimidin-2-yl}-isopropyl-amine (27 mg) as a yellow solid; LC-MS: tR=1.05 min, [M+H]+=442.81.

Workup

concentrationis concentrated
customThe crude product is purified on prep

Sources & evidence

ORD record: ord-a122746161c44cda8204fe85fb564ca7
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299086B2

Reaction notes

Loading…