Diisopropylethylamine → HCID 18354354, compound

HRID 429307Notes

Reaction equation

HRID 429307 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=4)=[CH:17][C:12]=3[N:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1.Cl.[CH3:26][O:27][C:28]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[C:32]([O:38][CH3:39])[C:29]=1[CH2:30][NH2:31].C(N(C(C)C)CC)(C)C>CS(C)=O.CCOC(C)=O.CCOCC>[CH3:1][S:2][C:3]1[N:8]=[C:7]([N:9]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][N:21]=[C:20]([NH:31][CH2:30][C:29]5[C:32]([O:38][CH3:39])=[CH:33][C:34]([O:36][CH3:37])=[CH:35][C:28]=5[O:27][CH3:26])[N:19]=4)=[CH:17][C:12]=3[N:11]=[CH:10]2)[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 162119141-(2,4,6-Trimethoxyphenyl)methanamine--hydrogen chloride (1/1)HCID 18354405HCID 18354405, compound

Product 1

HCID 18354354HCID 18354354, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21584169Diethylether ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2-methylthio-4-[5-(2-chloro-pyrimidin-4-yl)benzimidazol-1-yl]pyrimidine (EXAMPLE 34; 85 mg), 2,4,6-trimethoxybenzylamine hydrochloride (160 mg), and diisopropylethylamine (210 mL) in 3 mL of DMSO was heated to 100° C., at which point all solids were dissolved. The mixture was stirred at 100° C. for 20 h, then cooled and diluted with 15 mL of 1:1 EtOAc-Et2O, washed with 2×5 mL of water and 5 mL of brine, dried over Na2SO4 and concentrated. The residue was purified by preparative thin-layer chromatography) eluting with 95:5 CH2Cl2—MeOH to provide 98 mg of the title compound. Mass spectrum (ESI) 516.4 (M+1).

Workup

  1. dissolutionwere dissolved
  2. temperaturecooled
  3. washwashed with 2×5 mL of water and 5 mL of brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative thin-layer chromatography)
  7. washeluting with 95:5 CH2Cl2—MeOH

Sources & evidence

ORD record
ord-ff3c47ceeed546f2b74960f308b09baa
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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