3-Fluoroaniline → (2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)-(3-fluorophenyl)-amine

HRID 405917Notes

Reaction equation

HRID 405917 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.C(N(C(C)C)CC)(C)C.[F:21][C:22]1[CH:23]=[C:24]([NH2:28])[CH:25]=[CH:26][CH:27]=1>CN(C)C=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([F:21])[CH:23]=2)[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 97423-FluoroanilineHCID 81531DiisopropylethylamineHCID 457899672,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine

Product 1

HCID 59708433(2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)-(3-fluorophenyl)-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

4 g (II) are placed in 15 ml dimethylformamide, then 4.5 ml diisopropylethylamine and then 2.5 ml 3-fluorophenylamine are added. The reaction mixture is heated to 120° C., until there is no further reaction, and cooled, then evaporated down. The residue is mixed with water. The product is extracted with dichloromethane and purified by chromatography (silica gel, petroleum ether/ethyl acetate 80/20 to 60/40). 2.6 g (III-7) are obtained as a solid.

Workup

  1. customno further reaction
  2. temperaturecooled
  3. customevaporated down
  4. additionThe residue is mixed with water
  5. extractionThe product is extracted with dichloromethane
  6. custompurified by chromatography (silica gel, petroleum ether/ethyl acetate 80/20 to 60/40)
  7. custom2.6 g (III-7) are obtained as a solid

Sources & evidence

ORD record
ord-3fc25d45c909408cb50ca77e807d5f4b
Source dataset
uspto-grants-2014_06
Patent number
US08754073B2

Reaction notes

Loading…