Sodium hydride → Propanoic acid, 2,2-dimethyl-, (4-chloro-7H-pyrrolo(2,3-d)pyrimidin-7-yl)methyl ester

HRID 1615387Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].[C:13]([O:19][CH2:20]Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].[Cl-].[NH4+]>O1CCCC1>[C:13]([O:19][CH2:20][N:8]1[C:4]2[N:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]=2[CH:10]=[CH:9]1)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (100 mg, 0.651 mmol) was dissolved in tetrahydrofuran (5 mL). After cooling to 0° C., the reaction mixture was added to sodium hydride (60% in mineral oil, 52 mg, 1.30 mmol). 10 minutes later, chloromethyl pivalate (0.19 mL, 1.30 mmol) was added at 0° C. After stirring for 1.5 hours at room temperature, the reaction mixture was added to saturated ammonium chloride aqueous solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, EA:Hx=1:4) yielded (4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate (170 mg, 0.635 mmol) as white solid.

Workup

customThe organic layer was separated
extractionthe aqueous layer was extracted with ethyl acetate
washThe combined organic layer was washed with brine
dry with materialdried with magnesium sulfate
concentrationconcentrated under reduced pressure
customPurification of the residue by column chromatography (silica gel, EA:Hx=1:4)

Sources & evidence

ORD record: ord-bc4c7165972c488394f340a123f792fb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765749B2

Reaction notes

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