[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5](O)=[C:4]([O:10][C:11]2([CH2:14][OH:15])[CH2:13][CH2:12]2)[N:3]=1.[C:16]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH:13]1([CH:11]2[O:10][C:4]3[N:3]=[C:2]([Cl:1])[N:7]=[C:6]([Cl:8])[C:5]=3[O:15][CH2:14]2)[CH2:12][CH2:16]1To a solution of 2,4-dichloro-6-(1-hydroxymethyl-cyclopropoxy)-pyrimidin-5-ol (135 mg, 0.54 mmol) and triphenylphosphine (180 mg, 0.65 mmol) in THF (8 mL) was added DIAD (128 μL, 0.65 mmol) and the mixture stirred at RT for 30 minutes, then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, gradient 0-25% ethyl acetate in cyclohexane) affording 7-Cyclopropyl-2,4-dichloro-6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidine as a white solid (90 mg, 72%). 1H NMR (400 MHz, CDCl3): δ 4.30 (2H, s), 1.36-1.29 (2H, m), 1.01-0.95 (2H, m).
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