3-Methoxytyramine → 4-[2-(5-Chlorothieno[2,3-d]pyrimidin-4-ylamino)ethyl]-2-methoxyphenol

HRID 491266

Reaction equation

HRID 491266 reaction equation
Cl[C:2]1[C:3]2[C:10]([Cl:11])=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=1.C(N(CC)CC)C>CN(C=O)C.O>[Cl:11][C:10]1[C:3]2[C:2]([NH:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=3)=[N:7][CH:6]=[N:5][C:4]=2[S:8][CH:9]=1

Participants

6

Reactant 3

HCID 16693-MethoxytyramineHCID 8471TriethylamineHCID 157457684,5-Dichlorothieno[2,3-d]pyrimidine

Product 1

HCID 688569804-[2-(5-Chlorothieno[2,3-d]pyrimidin-4-ylamino)ethyl]-2-methoxyphenolYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4,5-dichlorothieno[2,3-d]pyrimidine (2.0 g, 9.8 mmol), 4-(2-aminoethyl)-2-methoxyphenol (1.8 g, 10.7 mmol) and triethylamine (1.2 g, 11.8 mmol) in DMF (15 mL) was stirred overnight. The solution was diluted with H2O and the product collected by filtration yielding an off white powder, 2.5 g, 7.4 mmol, 76 percent yield.

Workup

  1. filtrationthe product collected by filtration
  2. customyielding an off white powder, 2.5 g, 7.4 mmol, 76 percent yield

Sources & evidence

ORD record
ord-2815d09f82de493285b790fdf2f57820
Source dataset
uspto-grants-2009_05
Patent number
US07531482B2

Linked notes

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