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

HRID 1363243Notes

Reaction equation

HRID 1363243 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 a 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. 1H-NMR (300 MHz, CDCl3+10% CD3OD) δ 9.5 (s, 1H), 9.2 (s, 1H), 9.1 (s, 1H), 7.9 (d, 1H), 7.7 (d, 1H) ppm; MS (ESI), m/z 324 ([M+H]+).

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-3e44a1d4bfc548cd9cc4794b1e00697a
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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