Isopropanol → Pyrimidine, 2-chloro-4-(1-methylethoxy)-

HRID 1039917Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:15][CH:16]([OH:18])[CH3:17]>>[Cl:1][C:2]1[N:7]=[C:6]([O:18][CH:16]([CH3:17])[CH3:15])[CH:5]=[CH:4][N:3]=1

Participants

Reactant 3

HCID 3776Isopropanol

HCID 10796Cesium carbonate

HCID 775312,4-Dichloropyrimidine

Product 1

HCID 62338309Pyrimidine, 2-chloro-4-(1-methylethoxy)-Yield 41%

Procedure

To a solution of 2,4-dichloropyrimidine (5.0 g, 34 mmol) in 2-propanol (84 mL) was added Cs2CO3 (12 g, 37 mmol) and the mixture was stirred at rt for 16 h. The reaction was then heated to 65° C. for 3 h, after which time the reaction was filtered and concentrated. Purification on silica using a gradient solvent system of 0-10% EtOAc/Hexanes furnished 2-chloro-4-(propan-2-yloxy)pyrimidine (2.4 g, 41%) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 8.23 (d, J=5.7, 1H), 6.56 (d, J=5.7, 1H), 5.38 (hept, J=6.2, 1H), 1.34 (d, J=6.2, 6H).

Workup

temperatureThe reaction was then heated to 65° C. for 3 h
filtrationafter which time the reaction was filtered
concentrationconcentrated
customPurification on silica using a gradient solvent system of 0-10% EtOAc/Hexanes

Sources & evidence

ORD record: ord-19435d2b572b499babfcdca3769ec7fe
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551984B2

Reaction notes

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