Cyclopentylamine → 2-chloro-N-cyclopentyl-5-nitropyrimidin-4-amine

HRID 510161Notes

Reaction equation

HRID 510161 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])=[CH:19][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])=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 71472532-chloro-N-cyclopentyl-5-nitropyrimidin-4-amineYield 65.13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclopentylamine (5.17 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 (7.9 g) in a yield of 65.13%. 1H NMR (400 MHz, CDCl3): δ 9.03 (s, 1H), 8.38 (s, 1H), 4.59 (m, 1H), 2.13-2.21 (m, 2H), 1.72-1.85 (m, 4H), 1.53-1.71 (m, 2H) ppm.

Workup

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

Sources & evidence

ORD record
ord-4f778cf5b78c41fdbcbad5087885680a
Source dataset
uspto-grants-2015_08
Patent number
US09096601B2

Reaction notes

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