Methoxymethyl-triphenylphosphonium chloride → HCID 86618379, compound
Reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[Cl:29][C:30]1[N:31]=[C:32]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[C:33]2[S:38][C:37]([CH:39]=O)=[CH:36][C:34]=2[N:35]=1>C1COCC1>[Cl:29][C:30]1[N:31]=[C:32]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[C:33]2[S:38][C:37]([CH:39]=[CH:2][O:3][CH3:4])=[CH:36][C:34]=2[N:35]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
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).
Workup
- additionwas added dropwise
- stirringThe reaction mixture was stirred at room temperature for 16 h
- customquenched with water (80 mL)
- extractionextracted with ethyl acetate (2×80 mL)
- washThe combined organics were washed with aqueous brine solution (2×80 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- custompurified
Sources & evidence
- ORD record
- ord-5c78c51670034d29a3c3b9a33a25b57a
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450315B2
Reaction notes
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