Azidotrimethylsilane → HCID 90112960, compound

HRID 1509067Notes

Reaction equation

HRID 1509067 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][C:28]#[N:29])=[CH:23][CH:22]=3)[C:11]3[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][CH2:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.[N:30]([Si](C)(C)C)=[N+:31]=[N-:32].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][C:28]4[N:30]=[N:31][NH:32][N:29]=4)=[CH:23][CH:22]=3)[C:11]3[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][CH2:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 78378AzidotrimethylsilaneHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 90112476HCID 90112476, compound

Product 1

HCID 90112960HCID 90112960, compoundYield 70%

Conditions

Temperature
110 °C

Procedure

A 8-mL vial was charged with 2-[4-[[2-(3-Chlorophenyl)-5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl]amino]phenyl]acetonitrile (17 mg, 0.04 mmol, 1 eq.), azido(trimethyl)silane (0.2 ml, excess) and tetrabutylammonium fluoride hydrate (50 mg, 0.19 mmol, 4.6 eq.). The mixture was stirred at 110° C. overnight. After cooling to room temperature, the mixture was partitioned between dichloromethane (8 ml) and 2N HCl (4 ml). The organic layer was separated and washed with sodium bicarbonate solution (5 ml) and dried over Na2SO4. Removal of solvent under reduced pressure gave a residue, which was purified using a preparation TLC plate and 3% of methanol in dichloromethane as mobile to give the title compound as white solid (13 mg, 70% yield). MW=467.93. 1H NMR (400 MHz, methanol-d4) δ 8.32 (s, 1H), 8.24 (d, J=7.2 Hz, 1H), 7.67 (d, J=8.4 Hz, 2H), 7.46 (m, 2H), 7.38 (d, J=8.4 Hz, 2H), 4.38 (s, 2H), 3.63 (d, J=5.6 Hz, 2H), 3.14 (d, J=6.4 Hz, 2H), 2.54 (m, 2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between dichloromethane (8 ml) and 2N HCl (4 ml)
  3. customThe organic layer was separated
  4. washwashed with sodium bicarbonate solution (5 ml)
  5. dry with materialdried over Na2SO4
  6. customRemoval of solvent under reduced pressure
  7. customgave a residue, which
  8. customwas purified
  9. customa preparation TLC plate and 3% of methanol in dichloromethane as mobile

Sources & evidence

ORD record
ord-e59144a446204fb9899bbd5637afc32e
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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