Cyclohexanemethylamine → HCID 86691694, compound

HRID 510167Notes

Reaction equation

HRID 510167 reaction equation
[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[Cl:18][C:19]1[N:24]=[C:23](Cl)[C:22]([N+:26]([O-:28])=[O:27])=[CH:21][N:20]=1>ClCCl>[Cl:18][C:19]1[N:24]=[C:23]([NH:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:22]([N+:26]([O-:28])=[O:27])=[CH:21][N:20]=1

Participants

5

Reactant 3

HCID 76688CyclohexanemethylamineHCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 86691694HCID 86691694, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclohexylmethylamine (3.11 g) and N,N-diisopropylethylamine (6.2 ml) were dissolved into 45 ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitropyrimidine (4.85 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 20 min. Purification was conducted by a column chromatography to obtain a bright-yellow sheet-like solid (1.73 g) in a yield of 26%. ESI-MS (m/z, %) 272 (M−H)+. 1H NMR (400 MHz, CDCl3): δ 9.03 (s, 1H), 8.48 (s, 1H), 3.52 (m, 2H), 1.78-1.64 (m, 7H), 1.33-1.14 (m, 4H), 1.08-1.00 (m, 2H).

Workup

  1. additionAfter the completion of the dropwise addition
  2. customto react for 20 min
  3. customPurification

Sources & evidence

ORD record
ord-fcda96ac8e9d4b0f8c15b0fa8c43f4bb
Source dataset
uspto-grants-2015_08
Patent number
US09096601B2

Reaction notes

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