Diisopropylethylamine → Thieno[2,3-d]pyrimidine, 21a

온도

100 °C

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.380 g, 1.0 mmol) was added to 2-amino-4-phenyl-thieno[2,3-d]pyrimidine-6-carboxylic acid (0.187 g, 0.69 mmol). This mixture was suspended in dimethylformamide (DMF) (5.0 ml) and diisopropylethylamine (0.696 ml; 4.0 mmol) added to afford a yellow solution. Diethylamine hydrochloride (0.122 g; 5.0 mmol) was added and the reaction mixture was heated for ten minutes at 100° C. in a sealed vial in a microwave synthesiser. DMF was removed in vacuo and the residue was partitioned between ethyl acetate (30 ml) and water (30 ml). The phases were separated and the organic phase was washed with saturated sodium chloride solution and dried over sodium sulphate. Mixture was filtered and the filtrate solvents were removed in vacuo to leave a yellow solid which was adsorbed onto silica gel and purified by flash chromatography on silica gel (20 g), eluting with a solvent gradient of 15 to 50% ethyl acetate in hexane. This affords 2-amino-4-phenyl-thieno[2,3-d]pyrimidine-6-carboxylic acid ethylamide as a pale yellow solid (0.051 g; 25%).

1. customto afford a yellow solution
2. customDMF was removed in vacuo
3. customthe residue was partitioned between ethyl acetate (30 ml) and water (30 ml)
4. customThe phases were separated
5. washthe organic phase was washed with saturated sodium chloride solution
6. dry with materialdried over sodium sulphate
7. filtrationMixture was filtered
8. customthe filtrate solvents were removed in vacuo
9. customto leave a yellow solid which
10. custompurified by flash chromatography on silica gel (20 g)
11. washeluting with a solvent gradient of 15 to 50% ethyl acetate in hexane

ORD 기록

ord-7c4ee8e6a40e4c71b1fc53f4f50b9037

출처 데이터셋

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08642594B2