Cyclopentylamine → 2-Chloro-4-cyclopentylamino-5-nitro-6-methylpyrimidine

HRID 510162Notes

Reaction equation

HRID 510162 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([N+:24]([O-:26])=[O:25])=[C:19]([CH3:27])[N:18]=1>ClCCl>[Cl:16][C:17]1[N:22]=[C:21]([NH:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:20]([N+:24]([O-:26])=[O:25])=[C:19]([CH3:27])[N:18]=1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 81531DiisopropylethylamineHCID 2752942,4-Dichloro-6-methyl-5-nitropyrimidine

Product 1

HCID 71472772-Chloro-4-cyclopentylamino-5-nitro-6-methylpyrimidineYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclopentylamine (5.2 ml) and N,N-diisopropylethylamine (13.2 ml) were dissolved into 150 ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitro-6-methylpyrimidine (10.7 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 1 hour. Purification was conducted by a column chromatography to obtain a bright-yellow solid (11.2 g) in a yield of 84.8%. 1H NMR (400 MHz, CDCl3): δ 8.44 (s, 2H), 4.41 (m, 1H), 2.64 (s, 3H), 2.01-2.15 (m, 2H), 1.61-1.76 (m, 4H), 1.45-1.63 (m, 2H) ppm.

Workup

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

Sources & evidence

ORD record
ord-464bd4a6cbc7435291c0860118f6cf48
Source dataset
uspto-grants-2015_08
Patent number
US09096601B2

Reaction notes

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