Dibutyltin dichloride → HCID 66665218, compound

HRID 2176441Notes

Reaction equation

HRID 2176441 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[S:30][C:11]3=[N:12][C:13]([N:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[CH:14][C:15](=[O:16])[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[N:31]1[CH:36]=[CH:35][C:34]([CH:37]=O)=[CH:33][CH:32]=1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>O1CCCC1>[O:16]=[C:15]1[N:10]2[N:9]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][CH2:37][C:34]4[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=4)[CH:3]=3)[S:30][C:11]2=[N:12][C:13]([N:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:21][CH2:22]2)=[CH:14]1

Participants

6

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 133894-PyridinecarboxaldehydeHCID 66664953HCID 66664953, compound

Product 1

HCID 66665218HCID 66665218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl 4-(2-(3-aminophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (60 mg, 0.140 mmol, 1.0 equiv) and 4-pyridinecarboxaldehyde (0.013 mL, 0.140 mmol, 1.0 equiv) in 1 mL tetrahydrofuran in a microwave vial is added dibutyltin dichloride (4.25 mg, 0.014 mmol, 0.1 equiv) and Phenylsilane (0.035 mL, 0.280 mmol, 2.0 equiv). The mixture is heated in a microwave reactor for 10 min at 100° C. Upon completion, the reaction mixture is filtered through a thiol-SPE column (Stratospheres) and concentrated in vacuo to give crude tert-butyl 4-(5-oxo-2-(3-(pyridin-4-ylmethylamino)phenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate as a yellow oil. The residue is then taken on crude to the next reaction, which followed the same procedure as above to give 7-(piperazin-1-yl)-2-(3-(pyridin-4-ylmethylamino)phenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one (10 mg, 18%) as a white solid.

Workup

  1. filtrationUpon completion, the reaction mixture is filtered through a thiol-SPE column (Stratospheres)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff98c98b11d34f0bb9391139f6e66935
Source dataset
uspto-grants-2015_06
Patent number
US09066948B2

Reaction notes

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