HCID 86730178, compound → HCID 86730179, compound

HRID 1850142Notes

Reaction equation

HRID 1850142 reaction equation
[N:1]([CH:4]([C:6]1[N:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:9]=[CH:8][N:7]=1)[CH3:5])=[N+]=[N-]>CCO.[Pd]>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:10]2[CH:9]=[CH:8][N:7]=[C:6]([CH:4]([NH2:1])[CH3:5])[N:11]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 86730178HCID 86730178, compound

Product 1

HCID 86730179HCID 86730179, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(1-azidoethyl)-4-(4-fluorophenoxy)pyrimidine (120 mg, 0.463 mmol) was dissolved in 2 mL neat EtOH. 24.6 mg (0.023 mmol) of 10% Palladium on carbon catalyst was added. With vigorous stirring, the reaction vial was evacuated and purged 3 times with H2. The reaction vessel was fitted with an H2 balloon and stirred for 2 h. The mixture was filtered through Celite and concentrated in vacuo to give 75 mg (69%) 1-(4-(4-fluorophenoxy)pyrimidin-2-yl)ethanamine as a brown oil. 1H NMR (400 MHz, CDCl3) δ 8.45 (d, J=5.7 Hz, 1H), 7.13-6.92 (m, 4H), 6.59 (d, J=5.7 Hz, 1H), 4.00 (q, J=6.8 Hz, 1H), 1.34-1.30 (m, 3H). Anal. RP-HPLC tR=1.18 min. (Column=Inertsil C8 Column, 3.0 μm, 3.0×30 mm. Column Temperature=50° C. Eluents=A: Water (5 mM Ammonium formate, 2% ACN); B: ACN. Flow Rate=2 mL/min. Gradient=0 min 5% B; 5% to 95% B in 1.70 min; 0.3 min 95% B; 2.1 min 1% B.) MS m/z 234.2 (M+H)+.

Workup

  1. customWith vigorous stirring, the reaction vial was evacuated
  2. custompurged 3 times with H2
  3. customThe reaction vessel was fitted with an H2 balloon
  4. filtrationThe mixture was filtered through Celite
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59719184d73747f28573378d2bec5326
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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