Isopropanol → HCID 45275188, compound

HRID 1942892Notes

Reaction equation

HRID 1942892 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].[Na].Cl[C:7]1[N:12]=[C:11]([O:13][CH:14]([CH3:16])[CH3:15])[N:10]=[C:9]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[C:27]([CH3:29])[N:26]=[CH:25]3)=[C:20]([O:30][CH3:31])[CH:19]=2)[N:8]=1>O>[CH:2]([O:4][C:7]1[N:12]=[C:11]([O:13][CH:14]([CH3:16])[CH3:15])[N:10]=[C:9]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[C:27]([CH3:29])[N:26]=[CH:25]3)=[C:20]([O:30][CH3:31])[CH:19]=2)[N:8]=1)([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 5360545SodiumHCID 86640785HCID 86640785, compound

Product 1

HCID 45275188HCID 45275188, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2-propanol (321 mg, 5.34 mmol) was added metallic sodium (9 mg, 0.39 mmol). The resulting alcoholate-solution was treated with (4-chloro-6-isopropoxy-[1,3,5]triazin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine (100 mg, 0.27 mmol) and the resulting mixture refluxed for 3 hours. Water was added and the product extracted with ethyl acetate. The crude material was purified by chromatography on Si—NH2 gel (Isolute) using ethyl acetate as an eluent to give the title compound as a colorless solid (71 mg, 67%).

Workup

  1. temperaturethe resulting mixture refluxed for 3 hours
  2. extractionthe product extracted with ethyl acetate
  3. customThe crude material was purified by chromatography on Si—NH2 gel (Isolute)

Sources & evidence

ORD record
ord-68d5a74968b6469f9e2928205effc6d3
Source dataset
uspto-grants-2013_03
Patent number
US08389717B2

Reaction notes

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