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Diisopropylethylamine → 2-chloro-N-methyl-5-nitropyrimidin-4-amine

HRID 510158
Notes
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Reaction equation

HRID 510158 reaction equation
CN.C(O)C.[CH:6]([N:9](CC)C(C)C)(C)C.[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][N:17]=1>ClCCl>[Cl:15][C:16]1[N:21]=[C:20]([NH:9][CH3:6])[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][N:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 22028356Methylamine ethanol

Product 1

HCID 71472322-chloro-N-methyl-5-nitropyrimidin-4-amineYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl amine-ethanol (7.6 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 yellow solid (8.3 g) in a yield of 85.4%. 1H NMR (400 MHz, CDCl3): δ 9.05 (s, 1H), 8.41 (s, 1H), 3.22 (s, 3H) ppm.

Workup

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

Sources & evidence

ORD record
ord-075d87a7989c43cca1cf80dc2d258182
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096601B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes