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

HRID 1751798Notes

Reaction equation

HRID 1751798 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 are added followed by 2.5 ml 3-fluorophenylamine. The reaction mixture is heated to 120° C. until there is no further reaction then cooled and 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 in the form of a solid. Analytical HPLC (method A): RT=3.27 min

Workup

  1. customno further reaction
  2. temperaturethen cooled
  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 in the form of a solid

Sources & evidence

ORD record
ord-00f1449d59d84be9a08221e72c0bf1e5
Source dataset
uspto-grants-2015_10
Patent number
US09161927B2

Reaction notes

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