1,2-Dichloroethane → Isopropyl-{4-methyl-6-[3-(4-vinyl-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrimidin-2-yl}-amine

HRID 2069425Notes

Reaction equation

[CH:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[C:7]([CH3:14])[N:6]=1)([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.O[NH:30][C:31](=[NH:40])[C:32]1[CH:37]=[CH:36][C:35]([CH:38]=[CH2:39])=[CH:34][CH:33]=1>CN(C=O)C.O1CCOCC1.CCOC(C)=O>[CH:1]([NH:4][C:5]1[N:6]=[C:7]([CH3:14])[CH:8]=[C:9]([C:11]2[O:13][N:40]=[C:31]([C:32]3[CH:37]=[CH:36][C:35]([CH:38]=[CH2:39])=[CH:34][CH:33]=3)[N:30]=2)[N:10]=1)([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 95 °C

Procedure

To a suspension of 2-isopropylamino-6-methyl-pyrimidine-4-carboxylic acid (1.9 g, 11.8 mmol) in DMF (25 mL) is added HOBt (1.8 g, 13.4 mmol) followed by EDC (2.6 g, 13.4 mmol). The reaction mixture is stirred for 40 min until a clear solution is obtained and a solution of N-hydroxy-4-vinyl-benzamidine (2.09 g, 10.7 mmol) in DMF (20 mL) is added. After 2 h, EtOAc (320 mL) is added to the reaction mixture and the solution is then washed with sat. aq. NaHCO3 (3×100 mL), with brine, dried over MgSO4, filtered and evaporated to give a red oil. The oil is dissolved in dioxane (50 mL) and the solution is heated to 95° C. for 2 h. The reaction mixture is evaporated and purification by CC on silica gel affords the title compound as a yellow oil (2.79 g); LC-MS: tR=1.12; [M+H]+=321.95.

Workup

customis obtained
waitAfter 2 h
washthe solution is then washed with sat. aq. NaHCO3 (3×100 mL), with brine
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customto give a red oil
customThe reaction mixture is evaporated
custompurification by CC on silica gel

Sources & evidence

ORD record: ord-fbe9e60c8874461ea8981517758cc647
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299086B2

Reaction notes

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