Sodium hydride → HCID 178518221, compound
Reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].Cl[C:9]1[CH:18]=[N:17][C:16]2[C:15](=[O:19])[N:14]=[CH:13][NH:12][C:11]=2[CH:10]=1>>[CH:1]1([CH2:4][O:5][C:9]2[CH:18]=[N:17][C:16]3[C:15](=[O:19])[N:14]=[CH:13][NH:12][C:11]=3[CH:10]=2)[CH2:3][CH2:2]1Participants
Procedure
To a glass microwave reaction vessel (2-5 ml) were charged with cyclopropylmethanol (3.1 ml, 38.6 mmol) and sodium hydride (60% dispersion in mineral oil) (416 mg, 17.35 mmol). The reaction mixture was stirred at RT for several min. Finally 7-chloropyrido[3,2-d]pyrimidin-4(1H)-one (350 mg, 1.928 mmol) (from intermediate 11, step 1 & 2) was added, and the mixture was heated in a Initiator microwave reactor at 140° C. for 10 min. Then it was quenched with water and sat. NH4Cl and extracted with EtOAc for five times. The organic extract was washed with brine and dried over MgSO4. The solution was filtered and concentrated to give the crude material as a mixture. It was washed with Et2O and the brown solid was collected by filtration to yield 7-(cyclopropylmethoxy)pyrido[3,2-d]pyrimidin-4(1H)-one (50 mg, 0.230 mmol, 12% yield) as brown solid which was used for next step directly. MS m/z=218.1 (M+H).
Workup
- customTo a glass microwave reaction vessel (2-5 ml)
- temperaturethe mixture was heated in a Initiator microwave reactor at 140° C. for 10 min
- customThen it was quenched with water and sat. NH4Cl
- extractionextracted with EtOAc for five times
- extractionThe organic extract
- washwas washed with brine
- dry with materialdried over MgSO4
- filtrationThe solution was filtered
- concentrationconcentrated
- customto give the crude material as a mixture
- washIt was washed with Et2O
- filtrationthe brown solid was collected by filtration
Sources & evidence
- ORD record
- ord-fe935cabf2194e28ac2c3e5c36ea7172
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309263B2
Reaction notes
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