Water → HCID 86633623, compound

HRID 1855427Notes

Reaction equation

HRID 1855427 reaction equation
[O:1]1[CH2:4][CH:3]([OH:5])[CH2:2]1.CC([O-])(C)C.[K+].[Cl:12][C:13]1[N:18]=[C:17](Cl)[CH:16]=[C:15]([CH3:20])[N:14]=1.O>O1CCCC1.CCCCCCC.C(OCC)(=O)C.C(OCC)(=O)C>[Cl:12][C:13]1[N:14]=[C:15]([CH3:20])[CH:16]=[C:17]([O:5][CH:3]2[CH2:4][O:1][CH2:2]2)[N:18]=1

Participants

8

Reactant 4

HCID 962WaterHCID 794712,4-Dichloro-6-methylpyrimidineHCID 9942117Oxetan-3-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 86633623HCID 86633623, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of oxetan-3-ol (173 mg, 2.34 mmol) in 5 mL of tetrahydrofurane was treated with potassium tert-butylate (288 mg, 2.57 mmol) and stirred for 10 minutes at 20° C. 2,4-Dichloro-6-methylpyrimidine (381 mg, 2.34 mmol) was added and the resulting mixture stirred for 2 hours at 20° C. Addition of water and extraction with ethyl acetate, followed by chromatography on silica gel using heptane/ethyl acetate 7:3 v/v as a solvent gave the title compound as a yellowish foam (206 mg, 44%). MS ISP (m/e): 201.2 (33) [(M+H)+].

Workup

  1. stirringthe resulting mixture stirred for 2 hours at 20° C

Sources & evidence

ORD record
ord-083c80c9ab674998ad5011149cb56ac8
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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