HCID 89630016, compound → HCID 89630030, compound

HRID 882168Notes

Reaction equation

HRID 882168 reaction equation
[O:1]1[CH2:5][CH:4]=[CH:3][CH:2]1[C:6]1[C:14]2[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=3)=[N:12][CH:11]=[N:10][C:9]=2[N:8]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[CH:7]=1>CO.[Pd]>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[C:14]2[C:13]([C:15]3[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=3)[NH2:21])=[N:12][CH:11]=[N:10][C:9]=2[N:8]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[CH:7]=1

Participants

4

Reactant 1

HCID 89630016HCID 89630016, compound

Product 1

HCID 89630030HCID 89630030, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-(2,5-dihydrofuran-2-yl)-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (500 mg, 1.14 mmol) in methanol (6.0 mL), was added Pd/C (250 mg, 10 wt. % loading Pd). The atmosphere was purged with hydrogen gas and the resulting solution was stirred for 12 hours at room temperature under hydrogen atmosphere (1 atm). The reaction was then filtered and concentrated in vacuo to afford crude 3-(5-(tetrahydrofuran-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)aniline as a yellow oil. LRMS (ESI) calc'd for C22H31N4O2Si [M+H]+: 411, found 411. 1H NMR (400 MHz, CD3OD) δ 8.79 (d, J 3.2 Hz, 1H), 7.59 (s, 1H), 7.35-7.26 (m, 1H), 6.88-6.98 (m, 3H), 5.71 (s, 2H), 5.07-5.01 (m, 1H), 3.99-3.97 (m, 1H), 3.75-3.72 (m, 1H), 3.63-3.59 (m, 2H), 1.80-1.73 (m, 2H), 1.58-1.53 (m, 1H), 1.41-1.30 (m, 1H), 0.92-0.88 (m, 2H), 0.02 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-ca2fd84ad6564e089d40867f9d894cfa
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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