Water → (4-Benzyloxy-benzyl)-(5-chloro-pyrimidin-4-yl)-amine

HRID 2415107Notes

Reaction equation

HRID 2415107 reaction equation
CC([O-])(C)C.[K+].[Cl:7][C:8]1[C:9]([NH2:14])=[N:10][CH:11]=[N:12][CH:13]=1.[CH2:15]([O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>C(O)(C)(C)C>[CH2:15]([O:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][NH:14][C:9]2[C:8]([Cl:7])=[CH:13][N:12]=[CH:11][N:10]=2)=[CH:29][CH:30]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 700424-Benzyloxybenzyl chlorideHCID 226400505-Chloropyrimidin-4-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 22640031(4-Benzyloxy-benzyl)-(5-chloro-pyrimidin-4-yl)-amineYield 37%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

2.1 g (19 mmol) of potassium tert-butylate are added to a suspension of 2.2 g (17.2 mmol) of 5-chloro-pyrimidin-4-ylamine in tert-butanol (50 ml) and the temperature is kept at 60° C. After stirring for 1 h, a solution of 4.1 g (17.2 mmol) of 4-benzyloxy-benzyl chloride in tert-butanol (40 ml) is added dropwise and the reaction mixture is stirred at this temperature for 1 h. The reaction mixture is cooled to room temperature and poured into water (300 ml). The precipitate is filtered off and the filtrate is extracted with ethyl acetate (2×200 ml). The combined organic layers are dried with magnesium sulphate and concentrated in vacuo. The residue is purified by chromatography on silica gel (toluene/dioxane=6:1) to yield 2.0 g (37%) of the title compound as a beige powder of m.p. 95°-100° C.

Workup

  1. customis kept at 60° C
  2. stirringthe reaction mixture is stirred at this temperature for 1 h
  3. filtrationThe precipitate is filtered off
  4. extractionthe filtrate is extracted with ethyl acetate (2×200 ml)
  5. dry with materialThe combined organic layers are dried with magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by chromatography on silica gel (toluene/dioxane=6:1)

Sources & evidence

ORD record
ord-2d47bb43f9a448c89f505bf066a27683
Source dataset
uspto-grants-2004_11
Patent number
US06818642B2

Reaction notes

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