4-Chloro-5-(2,2-diethoxyethyl)-6-phenylpyrimidine → 2-(4-Chloro-6-phenylpyrimidin-5-yl)acetaldehyde

HRID 717579Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH2:8][CH:9](OCC)[O:10]CC)=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=[CH:4][N:3]=1>C1COCC1.Cl>[Cl:1][C:2]1[C:7]([CH2:8][CH:9]=[O:10])=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a stirred solution of 4-chloro-5-(2,2-diethoxyethyl)-6-phenylpyrimidine (800 mg) in dry THF (10 mL), concentrated HCl (2.0 mL) was added. The reaction mixture was stirred at 45° C. for 1 hour and solvents were removed under reduced pressure. The resulting oil was diluted with dichloromethane (50 mL), washed with 10% NaHCO3 (20 mL) and brine (20 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography using MeOH\CHCl3 (0.1:9.9) as eluent to afford 2-(4-chloro-6-phenylpyrimidin-5-yl)acetaldehyde (450 mg) as white solid. 1H NMR (DMSO-d6): δ 4.04 (s, 2H), 7.42-7.53 (m, 5H), 9.02 (s, 1H), 9.72 (s, 1H).

Workup

customsolvents were removed under reduced pressure
additionThe resulting oil was diluted with dichloromethane (50 mL)
washwashed with 10% NaHCO3 (20 mL) and brine (20 mL)
dry with materialThe organic layer was dried over anhydrous Na2SO4
concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-9089d5d7210147a89476be9f06b1bc67
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193725B2

Reaction notes

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