Tyramine → 4-[2-(6-Pyridin-3-yl-2-pyridin-2-yl-pyrimidin-4-ylamino)-ethyl]-phenol

HRID 1668656Notes

Reaction equation

HRID 1668656 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:3]=1.[NH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C>CC(O)C>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:6]2[N:5]=[C:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:3]=[C:2]([NH:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[CH:7]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 5610TyramineHCID 81531DiisopropylethylamineHCID 283091114-Chloro-2-(pyridin-2-yl)-6-(pyridin-3-yl)pyrimidine2×

Product 1

HCID 248628774-[2-(6-Pyridin-3-yl-2-pyridin-2-yl-pyrimidin-4-ylamino)-ethyl]-phenol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chloro-6-pyridin-3-yl-2-pyridin-2-yl-pyrimidine (Intermediate A) (1 eq, 0.74 mmol, 200 mg) and 4-(2-amino-ethyl)-phenol (1.2 eq, 0.89 mmol, 123 mg) are dissolved in iPrOH (3 ml). Then DIPEA (2 eq, 1.49 mmol, 196 mg) is added and the resulting mixture is heated using microwave radiation at 130° C. for 20 min. The solvent is removed in vacuo and the crude residue is purified by flash chromatography eluting with 0-5% MeOH in DCM yielding the title compound [M+H]+=370.

Workup

  1. temperaturethe resulting mixture is heated
  2. customat 130° C.
  3. customfor 20 min
  4. customThe solvent is removed in vacuo
  5. customthe crude residue is purified by flash chromatography
  6. washeluting with 0-5% MeOH in DCM yielding the title compound [M+H]+=370

Sources & evidence

ORD record
ord-37a0ec64cde5451e8daa021d053dc5f7
Source dataset
uspto-grants-2011_08
Patent number
US07989458B2

Reaction notes

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