Cyclohexylamine → HCID 7147236, compound

HRID 510166Notes

Reaction equation

HRID 510166 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[Cl:17][C:18]1[N:23]=[C:22](Cl)[C:21]([N+:25]([O-:27])=[O:26])=[CH:20][N:19]=1>ClCCl>[Cl:17][C:18]1[N:23]=[C:22]([NH:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:21]([N+:25]([O-:27])=[O:26])=[CH:20][N:19]=1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 7147236HCID 7147236, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclohexylamine (5.72 ml) and N,N-diisopropylethylamine (12.4 ml) were dissolved into 125 ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitropyrimidine (9.7 g) in dichloromethane (30 ml) at 0° C. After the completion of the dropwise addition, the mixture was kept at the same temperature to react for 80 min. Purification was conducted by a column chromatography to obtain a bright-yellow solid (9.1 g) in a yield of 71.2%. ESI-MS (m/z, %) 258 (M−H)+; 1H NMR (400 MHz, CDCl3): δ9.04 (s, 1H), 8.35 (s, 1H), 4.34 (m, 1H), 2.03 (m, 2H), 1.79 (m, 2H), 1.53-1.25 (m, 6H).

Workup

  1. additionAfter the completion of the dropwise addition
  2. customto react for 80 min
  3. customPurification

Sources & evidence

ORD record
ord-bf09d8bed41a455cab5936fdbc281660
Source dataset
uspto-grants-2015_08
Patent number
US09096601B2

Reaction notes

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