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

HRID 70088Notes

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

Participants

Conditions

Temperature: 120 °C

Procedure

4.00 g 2,4-dichloro-6,7-dihydro-thieno[3,2-d]pyrimidine are placed in 15 ml dimethylformamide, then first 4.50 ml diisopropylethylamine, then 2.50 ml 3-fluoro-aniline are added. The reaction mixture is stirred for 7 hours at 120° C., and after cooling evaporated down. The residue is extracted with dichloromethane and water, the organic phase is washed with saturated sodium chloride solution, dried and evaporated to dryness. The residue is purified by chromatography (NP_MPLC, Biotage cartridge (4*15 cm)). 2.60 g of the product are obtained as a powder.

Workup

temperatureafter cooling
customevaporated down
extractionThe residue is extracted with dichloromethane and water
washthe organic phase is washed with saturated sodium chloride solution
customdried
customevaporated to dryness
customThe residue is purified by chromatography (NP_MPLC, Biotage cartridge (4*15 cm))

Sources & evidence

ORD record: ord-352e0c13adbe449d8b807c014ed1ce55
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822474B2

Reaction notes

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