Allyl Alcohol → HCID 77230955, compound

HRID 869283Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([O:9][CH3:10])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:17]([OH:20])[CH:18]=[CH2:19]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([O:20][CH2:17][CH:18]=[CH2:19])[C:5]([O:9][CH3:10])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2,4-dichloro-5-methoxypyrimidine (85 g, 475 mmol), and K2CO3 (78.8 g, 570 mmol) in allyl alcohol (320 mL, 4.75 mol) was heated to 70° C. for 5 h before being cooled to r.t. and diluted with DCM, filtered through Celite (DCM wash) and concentrated to give 95.0 g (99.7%) of 2-chloro-5-methoxy-4-(prop-2-en-1-yloxy)pyrimidine. 1H-NMR (CDCl3, 300 MHz) δ 7.85 (s, 1H), 6.09-5.99 (m, 1H), 5.43-5.38 (m, 1H), 5.31-5.27 (m, 1H), 4.91 (m, 2H), 3.87 (s, 3H). MS (ESI) m/z (M+H)+ 201.0.

Workup

temperaturebefore being cooled to r.t.
filtrationfiltered through Celite (DCM wash)
concentrationconcentrated

Sources & evidence

ORD record: ord-a5ab78611e8d4e7e8771347d6a15edfb
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969364B2

Reaction notes

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