Isopropylamine → 2-Chloro-N-(1-methylethyl)-5-nitro-4-pyrimidinamine

HRID 510159Notes

Reaction equation

HRID 510159 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].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]([CH3:3])[CH3:2])[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 71472352-Chloro-N-(1-methylethyl)-5-nitro-4-pyrimidinamineYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Isopropylamine (4.5 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-nitropyrimidine (10.0 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 half an hour. Purification was conducted by a column chromatography to obtain a bright-yellow solid (10.1 g) in a yield of 90.4%. 1H NMR (400 MHz, CDCl3): δ 9.03 (s, 1H), 8.24 (s, 1H), 4.53 (m, 1H), 1.34 (d, J=6.8 Hz, 6H) ppm.

Workup

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

Sources & evidence

ORD record
ord-a416e04b5211453db0d1bbb57ccc9376
Source dataset
uspto-grants-2015_08
Patent number
US09096601B2

Reaction notes

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