HCID 89629895, compound → HCID 89630065, compound

HRID 882175Notes

Reaction equation

HRID 882175 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:7]2[C:15]3[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=4)=[N:13][CH:12]=[N:11][C:10]=3[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:8]=2)=[N:5][N:6]=1>CO>[CH3:1][C:2]1[S:3][C:4]([C:7]2[C:15]3[C:14]([C:16]4[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=4)[NH2:22])=[N:13][CH:12]=[N:11][C:10]=3[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[CH:8]=2)=[N:5][N:6]=1

Participants

3

Reactant 1

HCID 89629895HCID 89629895, compound

Product 1

HCID 89630065HCID 89630065, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-5-(4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-1,3,4-thiadiazole (0.38 g, 0.81 mmol) in methanol (10 mL) was added Pt (1% on C, V doped) (343 mg). The atmosphere was purged with hydrogen and the solution was stirred for 4 hours at room temperature under hydrogen atmosphere (1 atm). The reaction was then filtered and concentrated in vacuo to afford crude 3-(5-(5-methyl-1,3,4-thiadiazol-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)aniline as a dark green solid. LRMS (ESI) calc'd for C21H27N6O3SSi [M+H]+: 439, found 439.

Workup

  1. customThe atmosphere was purged with hydrogen
  2. filtrationThe reaction was then filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab132837b80243bbbe4d64974575334a
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

Loading…