Iodoethane → 4-Chloro-5-ethyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one

HRID 1685176

Reaction equation

[Cl:1][C:2]1[C:3]2[CH2:10][C:9](=[O:11])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:22](I)[CH3:23]>C1COCC1>[Cl:1][C:2]1[C:3]2[CH:10]([CH2:22][CH3:23])[C:9](=[O:11])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Add 4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (0.5 g; 0.0029 mol; 1.0 equiv) in THF (20 mL) and cool to −78° C. under argon atmosphere. Add drop-wise lithium hexamethyl-disilazide (5.89 mL, 0.0059 mol; 2.0 equiv; 1 M in THF). Stir at −78° C. for 30 min. Add drop-wise ethyl iodide (0.48 mL; 0.0059 mol; 2.0 equiv) and allow the reaction temperature to come to 0° C. slowly. Stir for 4 h. Quench with saturated ammonium chloride aqueous and extract with EA. Evaporate the organic layer to get the title compound (0.24 g; 41.38%).

Workup

customto come to 0° C.
stirringStir for 4 h
customQuench with saturated ammonium chloride aqueous
extractionextract with EA
customEvaporate the organic layer

Sources & evidence

ORD record: ord-b8d34e63e89f430d8c8aa720f0db1e55
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148387B2

Linked notes

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