Dimethylformamide → 2-Chloro-4-morpholinofuro[3,2-d]pyrimidine-6-carbaldehyde

HRID 390814Notes

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.CN([CH:25]=[O:26])C>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]([CH:25]=[O:26])=[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 (40 mg, 1.0 eq) dissolved in THF (1.7 ml) at −78° C. was added 1.6M solution of n-butyllithium (0.14 ml, 1.3 eq, 1.6M in hexanes). Reaction mixture was stirred at −78° C. for 30 minutes. DMF (0.05 ml, 4.0 eq) was added and reaction mixture was allowed to slowly warm up to room temperature and stirred for 90 minutes. Reaction mixture was quenched with water, 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-4-morpholinofuro[3,2-d]pyrimidine-6-carbaldehyde 39 (22 mg, 50%): 1H NMR (CDCl3, 400 MHz) δ 9.92 (s, 1H), 7.48 (s, 1H), 4.12 (m, 4H), 3.86 (dd, 4H); MS (Q1) 268 (M)+.

Workup

customReaction mixture
customreaction mixture
temperatureto slowly warm up to room temperature
stirringstirred for 90 minutes
customReaction mixture
customwas quenched with water
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-04d25a93cad54a419b1b79589362be61
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383620B2

Reaction notes

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