Triethylsilane → 2-(6-Cyano-1H-benzimidazol-1-yl)-5-nitropyrimidin-4-yl thiocyanate

HRID 605860Notes

Reaction equation

HRID 605860 reaction equation
COC1C=C(OC)C=CC=1[CH2:5][NH:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[NH:15][C:16]1[N:21]=[C:20]([S:22][C:23]#[N:24])[C:19]([N+:25]([O-:27])=[O:26])=[CH:18][N:17]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N+:25]([C:19]1[C:20]([S:22][C:23]#[N:24])=[N:21][C:16]([N:15]2[C:8]3[CH:9]=[C:10]([C:11]#[N:12])[CH:13]=[CH:14][C:7]=3[N:6]=[CH:5]2)=[N:17][CH:18]=1)([O-:27])=[O:26]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 566052112-(5-Cyano-2-{[(2,4-dimethoxyphenyl)methyl]amino}anilino)-5-nitropyrimidin-4-yl thiocyanate

Product 1

HCID 533895902-(6-Cyano-1H-benzimidazol-1-yl)-5-nitropyrimidin-4-yl thiocyanateYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To the solution of 0.58 g (1.25 mmol) 4-(2,4-dimethoxybenzylamino)-3-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)benzonitrile in 10 mL 30% (v/v) TFA in DCM was added 0.01 mL of triethylsilane. The mixture was stirred for 0.5 hr. LCMS indicated the completion of de-protection. A red residue was obtained after removing the volatiles on rotary evaporator, and was suspended (majority dissolved) in 10 mL 1:1 trimethyl orthoformate: MeOH. The resulting mixture was stirred for 2 hrs at room temperature. Yellow solids were precipitated. Desired product (0.38 g, 95% overall yield) was obtained after suction filtration and washing with cold MeOH twice.

Workup

  1. customA red residue was obtained
  2. customafter removing the volatiles
  3. customon rotary evaporator
  4. dissolution(majority dissolved) in 10 mL 1:1 trimethyl orthoformate
  5. stirringThe resulting mixture was stirred for 2 hrs at room temperature
  6. customYellow solids were precipitated

Sources & evidence

ORD record
ord-0fcce1e5687c4e7f826ae899dca753b3
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

Loading…