2-(4-Aminophenyl)ethylamine → [2-(4-Amino-phenyl)-ethyl]-thieno[3,2-d]pyrimidin-4-yl-amine

HRID 1818922Notes

Reaction equation

HRID 1818922 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.Cl[C:12]1[C:13]2[S:20][CH:19]=[CH:18][C:14]=2[N:15]=[CH:16][N:17]=1.CCN(C(C)C)C(C)C>C(O)CCC>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:1][C:12]2[C:13]3[S:20][CH:19]=[CH:18][C:14]=3[N:15]=[CH:16][N:17]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 728952-(4-Aminophenyl)ethylamine2×HCID 81531DiisopropylethylamineHCID 27358214-Chlorothieno[3,2-d]pyrimidine

Product 1

HCID 61220421[2-(4-Amino-phenyl)-ethyl]-thieno[3,2-d]pyrimidin-4-yl-amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4-(2-amino-ethyl)-phenylamine (compound 12.1; 0.1 mmol.), compound 6.2 (1.0 equivalent) and DIEA (2.5 equivalents) was heated in n-butanol (2 mL) at 135° C. for 2 hours. The reaction mixture was cooled and partitioned between dichloromethane and water. The organic layer was separated, washed with brine, dried and concentrated under reduced pressure to give crude [2-(4-amino-phenyl)-ethyl]-thieno[3,2-d]pyrimidin-4-yl-amine (compound 12.2) which was used without purification for the next step.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between dichloromethane and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd2ee212e55e439289c2bf5e09357293
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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