Diisopropylethylamine → 5-chloro-N4-(6-methoxyhexahydrofuro[3,2-b]furan-3-yl)-N2-(1-methyl-1H-pyrazol-4-yl)pyrimidine-2,4-diamine

HRID 1053936Notes

Reaction equation

HRID 1053936 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:13][O:12][CH:11]3[CH:14]([O:17][CH3:18])[CH2:15][O:16][CH:10]23)[C:5]([Cl:19])=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.Cl.[CH3:30][N:31]1[CH:35]=[C:34]([NH2:36])[CH:33]=[N:32]1>CCCCO>[Cl:19][C:5]1[C:6]([NH:8][CH:9]2[CH2:13][O:12][CH:11]3[CH:14]([O:17][CH3:18])[CH2:15][O:16][CH:10]23)=[N:7][C:2]([NH:36][C:34]2[CH:33]=[N:32][N:31]([CH3:30])[CH:35]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 173542681-methyl-1H-pyrazol-4-amineHCID 1183879912,5-dichloro-N-(6-methoxyhexahydrofuro[3,2-b]furan-3-yl)pyrimidin-4-amine

Product 1

HCID 1183879535-chloro-N4-(6-methoxyhexahydrofuro[3,2-b]furan-3-yl)-N2-(1-methyl-1H-pyrazol-4-yl)pyrimidine-2,4-diamineYield 42.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2,5-dichloro-N-(6-methoxyhexahydrofuro[3,2-b]furan-3-yl)pyrimidin-4-amine (430 mg, 1.4046 mmol), DIPEA (546.7 mg, 4.23 mmol) and 1-methylpyrazol-4-amine hydrochloride (283.3 mg, 2.12 mmol) in n-BuOH (10 mL) was stirred in a sealed tube at 150° C. for 23 h. The reaction solution was concentrated in vacuo, and the residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1) to give the crude product as a white solid. The crude product was recrystallized from acetone to give the title compound as a white solid (220 mg, 42.6%).

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customthe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1)
  3. customto give the crude product as a white solid
  4. customThe crude product was recrystallized from acetone

Sources & evidence

ORD record
ord-1a64800943d04ad6853b380969613849
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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