Diisopropylethylamine → Methyl 4-(2-chloro-5-nitropyrimidin-4-yl)-3-methylmorpholine-3-carboxylate

HRID 1695995Notes

Reaction equation

[CH3:1][C:2]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][O:6][CH2:5][CH2:4][NH:3]1.[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[Cl:12][C:13]1[N:18]=[C:17]([N:3]2[CH2:4][CH2:5][O:6][CH2:7][C:2]2([CH3:1])[C:8]([O:10][CH3:11])=[O:9])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=1

Participants

Conditions

Temperature: -10 °C

Procedure

Methyl 3-methylmorpholine-3-carboxylate (4.21 g, 26.4 mmol) was dissolved in THF (60 ml) to form a clear solution. 2,4-Dichloro-5-nitropyrimidine (5.13 g, 26.4 mmol) was added and the solution was cooled to −10° C. Diisopropylethylamine (6.93 ml, 39.7 mmol) was added while the temperature was maintained at −8 to −10° C. The reaction was stirred for 4 hours at 0° C. and for 16 hours at room temperature. The solvent was removed under reduced pressure. EtOAc (120 ml) was added and the mixture was washed with water (3×30 ml). The organic solution was concentrated to afford 8.4 g of crude methyl 4-(2-chloro-5-nitropyrimidin-4-yl)-3-methylmorpholine-3-carboxylate as an oil. The crude material was used in the next step without further purification. MS [M+H] calculated for C11H13ClN4O5, 317. found, 317.

Workup

customto form a clear solution
temperaturewas maintained at −8 to −10° C
customThe solvent was removed under reduced pressure
additionEtOAc (120 ml) was added
washthe mixture was washed with water (3×30 ml)
concentrationThe organic solution was concentrated

Sources & evidence

ORD record: ord-2e662abb3b044fa499735516683ba506
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163755B2

Reaction notes

Loading…