Diisopropylethylamine → 2-{6-Butyl-2-[4-(4-trifluoromethoxyphenyl) imidazol-1-yl] pyrimidin-4-ylamino}-4-methyl-pentanoic acid tert-butyl ester

HRID 1822798Notes

Reaction equation

Cl.[C:2]([O:6][C:7](=[O:14])[C@H:8]([CH2:10][CH:11]([CH3:13])[CH3:12])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(C(C)C)CC)(C)C.[CH2:24]([C:28]1[CH:33]=[C:32](Cl)[N:31]=[C:30]([N:35]2[CH:39]=[C:38]([C:40]3[CH:45]=[CH:44][C:43]([O:46][C:47]([F:50])([F:49])[F:48])=[CH:42][CH:41]=3)[N:37]=[CH:36]2)[N:29]=1)[CH2:25][CH2:26][CH3:27]>CS(C)=O>[C:2]([O:6][C:7](=[O:14])[CH:8]([NH:9][C:32]1[CH:33]=[C:28]([CH2:24][CH2:25][CH2:26][CH3:27])[N:29]=[C:30]([N:35]2[CH:39]=[C:38]([C:40]3[CH:45]=[CH:44][C:43]([O:46][C:47]([F:48])([F:49])[F:50])=[CH:42][CH:41]=3)[N:37]=[CH:36]2)[N:31]=1)[CH2:10][CH:11]([CH3:12])[CH3:13])([CH3:5])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

L-Leucine tert-butyl ester hydrochloride (291 mg) was dissolved in DMSO (5 mL) under an argon atmosphere and treated with diisopropylethylamine (450 μL, 2.6 mmol, 4 eq.) followed by 4-Butyl-6-chloro-2-[4-(4-trifluoromethoxy-phenyl)-imidazol-1-yl]-pyrimidine (274 mg). The mixture was heated to 80° C. for 48 h. DMSO and the volatiles were removed in vacuo to give a crude residue from which 2-{6-butyl-2-[4-(4-trifluoromethoxyphenyl) imidazol-1-yl] pyrimidin-4-ylamino}-4-methyl-pentanoic acid tert-butyl ester (321 mg) was isolated by flash chromatography (n-hexanes/ethyl acetate 4/1).

Workup

customDMSO and the volatiles were removed in vacuo

Sources & evidence

ORD record: ord-0921f708d1e2476fbf241dc95e1bddce
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037916B2

Reaction notes

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