Triethylamine → (R)-(4-(4-amino-5-nitropyrimidin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanone

HRID 931318Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.Cl.[NH:13]1[CH2:18][CH2:17][O:16][C@@H:15]([C:19]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[CH2:14]1.C(N(CC)CC)C>C(#N)C>[NH2:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=[C:2]([N:13]2[CH2:18][CH2:17][O:16][C@@H:15]([C:19]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:20])[CH2:14]2)[N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-Chloro-5-nitropyrimidin-4-amine (106 mg, 0.612 mmol) was added to a solution of (R)-morpholin-2-yl(pyrrolidin-1-yl)methanone hydrochloride (0.15 g, 0.68 mmol) and triethylamine (0.28 mL, 2.04 mmol) in acetonitrile (10 mL) at room temperature. The reaction mixture was heated at 80° C. for 1 h, then was cooled to room temperature and stirred for 12 h. The solvent was removed under reduced pressure and the resulting crude material was triturated with diethyl ether to afford (R)-(4-(4-amino-5-nitropyrimidin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanone (0.11 g). MS (ES+APCI) (M+H) 323.1; LCMS retention time: 3.518 min (Method S1).

Workup

temperaturewas cooled to room temperature
customThe solvent was removed under reduced pressure
customthe resulting crude material was triturated with diethyl ether

Sources & evidence

ORD record: ord-53fa0c8771d746528d4ca7355c52d881
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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