Diisopropylethylamine → HCID 178526829, compound

HRID 715636Notes

Reaction equation

HRID 715636 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][N:3]=1.[NH2:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20][CH2:19]1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:9]1([NH:8][C:6]2[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][N:3]=[C:2]([NH:17][C@H:18]3[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20][CH2:19]3)[N:7]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 71472532-chloro-N-cyclopentyl-5-nitropyrimidin-4-amineHCID 178511715HCID 178511715, compound

Product 1

HCID 178526829HCID 178526829, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2-Chloro-5-nitropyrimidin-4-yl)cyclopentylamine (6.18 mmol, 1.5 g.) and trans-4-aminocyclohexan-1-ol (7.42 mmol, 854 mg mL) were mixed in DMF (18 mL) and N,N-diisopropylethylamine (7.42 mmol, 1.29 mL) was added. The reaction mixture was stirred overnight. Solvent was removed in vacuo and the residue purified using column chromatography (SiO2, 1:1 n-hexanes/ethyl acetate→7:3 n-hexanes/ethyl acetate→ethyl acetate) to give the desired product (1.75 g, 88% yield). ES-MS: 322 (M+1). When the hydrochloride salt of an amine is used in place of the trans-4-aminocyclohexan-1-ol described above, 2 to 3 equivalents of N,N-diisopropylethylamine or sodium bicarbonate and tetrahydrofuran or acetonitrile were used as solvent.

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue purified

Sources & evidence

ORD record
ord-b011901f35474a6cb69b4dc598d53f7f
Source dataset
uspto-grants-2015_11
Patent number
US09187479B2

Reaction notes

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