Cyclopropylamine → HCID 24903951, compound

HRID 510160Notes

Reaction equation

HRID 510160 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[Cl:14][C:15]1[N:20]=[C:19](Cl)[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][N:16]=1>ClCCl>[Cl:14][C:15]1[N:20]=[C:19]([NH:4][CH:1]2[CH2:3][CH2:2]2)[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 24903951HCID 24903951, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclopropylamine (1.8 ml) and N,N-diisopropylethylamine (6.6 ml) were dissolved into 75 ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitropyrimidine (5.0 g) in dichloromethane (15 ml) at 0° C. After the completion of the dropwise addition, the mixture was kept at the same temperature to react for 40 min. Purification was conducted by a column chromatography to obtain a bright-yellow solid (2.6 g) in a yield of 47%. 1H NMR (400 MHz, CDCl3): δ 8.84 (s, 1H), 7.35 (s, 1H), 3.84 (m, 1H), 1.36 (m, 4H) ppm.

Workup

  1. additionAfter the completion of the dropwise addition
  2. customto react for 40 min
  3. customPurification

Sources & evidence

ORD record
ord-2a087df0a17f4b3cbf2fefb3c248a3ba
Source dataset
uspto-grants-2015_08
Patent number
US09096601B2

Reaction notes

Loading…