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

HRID 449855Notes

Reaction equation

HRID 449855 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 followed by 2.5 ml 3-fluoro-phenylamine are added. The reaction mixture is heated to 120° C. until there is no further reaction and after cooling 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-3) are obtained as a solid.

Workup

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

Sources & evidence

ORD record
ord-a929c4a1a7bf414794f9ef8bc8947d08
Source dataset
uspto-grants-2013_07
Patent number
US08486948B2

Reaction notes

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