Iodine → 2-Chloro-6-iodo-4-morpholinofuro[3,2-d]pyrimidine

HRID 2098619Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C([Li])CCC.[I:22]I>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[O:10][C:9]([I:22])=[CH:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-chloro-4-morpholinofuro[3,2-d]pyrimidine 38 (50 mg, 1.0 eq) dissolved in THF (2.1 ml) at −78° C. was added 1.6M solution of n-butyllithium (0.17 ml, 1.3 eq, 1.6M in hexanes). Reaction mixture was stirred at −78° C. for 30 minutes. A solution of iodine (159 mg, 3.0 eq) in THF (0.6 ml) was added and reaction mixture was allowed to slowly warm up to room temperature and stirred for 45 minutes. The reaction mixture was quenched with saturated aq. Na2S2O3, and extracted with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated. The crude reaction mixture was purified by flash chromatography to yield 2-chloro-6-iodo-4-morpholinofuro[3,2-d]pyrimidine 45 (63 mg, 83%): MS (Q1) 366 (M)+.

Workup

customReaction mixture
customreaction mixture
temperatureto slowly warm up to room temperature
stirringstirred for 45 minutes
customThe reaction mixture was quenched with saturated aq. Na2S2O3
extractionextracted with dichloromethane
dry with materialThe combined organic layers were dried (Na2SO4)
concentrationconcentrated
customThe crude reaction mixture
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-adcc2aa4906b4440a7500bc2e4bee757
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450315B2

Reaction notes

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