Acetic Acid → HCID 58174068, compound

HRID 1255879Notes

Reaction equation

HRID 1255879 reaction equation
[C:1]([C:3]1[C:4]([N:9]=[CH:10][N:11](C)C)=[N:5][CH:6]=[CH:7][N:8]=1)#[N:2].N[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C(O)(=O)C>C(O)C>[N:9]1[C:4]2[C:3](=[N:8][CH:7]=[CH:6][N:5]=2)[C:1]([NH:2][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5610TyramineHCID 12686527HCID 12686527, compound

Product 1

HCID 58174068HCID 58174068, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N′-(3-cyanopyrazin-2-yl)-N,N-dimethylformamidine (prepared as in Albert and Ohta, J. Chem. Soc. C 1971, 3727-3730, which is expressly incorporated by reference herein; 2.0 g, 11.4 mmol) in ethyl alcohol (EtOH; 50 mL) was added 4-(2-aminoethyl)-phenol (4.7 g, 34 mmol) and acetic acid (3.9 mL, 4.1 g, 68 mmol). The solution was heated to reflux for 19 h, concentrated in vacuo, and the residue was slurried with H2O and suction filtered. The filter cake was washed with H2O and dried in a vacuum oven (80° C., 0.5 torr) to yield 4-[2-(pteridin-4-ylamino)-ethyl]-phenol (2.7 g) as a white solid: mp>210° C.; 1H NMR (DMSO-d6) δ 9.20 (s, 1H), 9.08 (s, 1H), 8.94 (s, 1H), 8.95 (t, J=6.0 Hz, 1H), 8.82 (s, 1H), 8.64 (s, 1H), 7.06 (d, J=8.5 Hz, 2H), 6.69 (d, J=8.2 Hz, 2H), 3.75 (t, J=6.2 Hz, 2H), 2.85 (t, J=7.6 Hz, 2H); ESIMS m/z 268 (M+).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 19 h
  3. concentrationconcentrated in vacuo
  4. filtrationfiltered
  5. washThe filter cake was washed with H2O
  6. customdried in a vacuum oven (80° C., 0.5 torr)

Sources & evidence

ORD record
ord-4474e5fe4a744484b95431cac2bf8261
Source dataset
uspto-grants-2013_06
Patent number
US08461164B2

Reaction notes

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