Methoxymethyl-triphenylphosphonium chloride → HCID 86618379, compound

Temperature

0 °C

To a suspension of methoxymethyl triphenylphosphonium chloride (7.24 g) in THF (100 mL) at 0° C. was added n-butyllithium (6.76 mL of a 2.M solution in hexanes). The reaction mixture was stirred at 0° C. for 1 h and then a suspension of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde 10 (2 g) in THF (30 mL) was added dropwise. The reaction mixture was stirred at room temperature for 16 h and then quenched with water (80 mL) and extracted with ethyl acetate (2×80 mL). The combined organics were washed with aqueous brine solution (2×80 mL), dried (MgSO4), concentrated and purified using column chromatography to give 2-chloro-6-(2-methoxy-vinyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (mixture of cis/trans isomers) as a yellow solid (2.24 g).

1. additionwas added dropwise
2. stirringThe reaction mixture was stirred at room temperature for 16 h
3. customquenched with water (80 mL)
4. extractionextracted with ethyl acetate (2×80 mL)
5. washThe combined organics were washed with aqueous brine solution (2×80 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated
8. custompurified

ORD record

ord-19ea285f0f514f61b6d0f1b2c01d6c8d

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07846929B2