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

HRID 2069425
Notes
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Reaction equation

HRID 2069425 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 669337152-(Isopropylamino)-6-methylpyrimidine-4-carboxylic acidHCID 178436434HCID 178436434, compound

Product 1

HCID 68509545Isopropyl-{4-methyl-6-[3-(4-vinyl-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrimidin-2-yl}-amineYield 81.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

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

  1. customis obtained
  2. waitAfter 2 h
  3. washthe solution is then washed with sat. aq. NaHCO3 (3×100 mL), with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a red oil
  8. customThe reaction mixture is evaporated
  9. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes