Triethylamine → 2,5-dichloro-N-(6-methoxyhexahydrofuro[3,2-b]furan-3-yl)pyrimidin-4-amine

HRID 1053935Notes

Reaction equation

HRID 1053935 reaction equation
[CH3:1][O:2][CH:3]1[CH:7]2[O:8][CH2:9][CH:10]([NH2:11])[CH:6]2[O:5][CH2:4]1.C(N(CC)CC)C.[Cl:19][C:20]1[N:25]=[C:24](Cl)[C:23]([Cl:27])=[CH:22][N:21]=1>CCO>[Cl:19][C:20]1[N:25]=[C:24]([NH:11][CH:10]2[CH2:9][O:8][CH:7]3[CH:3]([O:2][CH3:1])[CH2:4][O:5][CH:6]23)[C:23]([Cl:27])=[CH:22][N:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 756144396-Methoxyhexahydrofuro[3,2-b]furan-3-amine

Product 1

HCID 1183879912,5-dichloro-N-(6-methoxyhexahydrofuro[3,2-b]furan-3-yl)pyrimidin-4-amineYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-methoxyhexahydrofuro[3,2-b]furan-3-amine (380 mg, 2.3872 mmol) in EtOH (25 mL) were added N,N-diethylethanamine (967.4 mg, 9.560 mmol) and 2,4,5-trichloropyrimidine (526.2 mg, 2.869 mmol). The reaction was stirred at rt for 4 h, then concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=2/1) to give a white solid (490 mg, 67.2%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=2/1)

Sources & evidence

ORD record
ord-d3491c8ae53845e19f5fc1e06eae0add
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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