Cyclopropylamine → HCID 24903951, compound

HRID 552108Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.C([N:15](CC)[CH:16]([CH3:18])[CH3:17])(C)C.C1(N)CC1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:15][CH:16]2[CH2:18][CH2:17]2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To 10.0 g (53 mmol, 1.0 eq.) of 2,4-dichloro-5-nitropyrimidine in 40 mL of THF at −78° C. was added 22 mL (120 mmol, 2.2 eq.) of N,N-diisopropylethylamine and 3.7 mL (53 mmol, 1.0 eq.) of cyclopropylamine. The reaction mixture was stirred at −78° C. for 30 min and then allowed to warm to room temperature and stirred for an additional 1 h. The solvent was removed in vacuo to afford a yellow solid. The product was purified by flash chromatography (15% EtOAc/hexanes) to provide 8.8 g (8.1 mmol, 77%) of 2-chloro-N-cyclopropyl-5-nitropyrimidin-4-amine (I-1) as a yellow solid.

Workup

temperatureto warm to room temperature
stirringstirred for an additional 1 h
customThe solvent was removed in vacuo
customto afford a yellow solid
customThe product was purified by flash chromatography (15% EtOAc/hexanes)

Sources & evidence

ORD record: ord-1dfcc1f9b9004daea47a7f63aa05e7ea
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951803B2

Reaction notes

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