Triethylamine → (1S-cis)-4-[[6-Chloro-5-nitro-2-(propylthio)-pyrimidin-4-yl]amino]-2-cyclopentene-1-ol

HRID 1069027Notes

Reaction equation

HRID 1069027 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([S:12][CH2:13][CH2:14][CH3:15])[N:3]=1.C(N(CC)CC)C.[NH2:23][C@@H:24]1[CH2:28][C@H:27]([OH:29])[CH:26]=[CH:25]1>O1CCCC1.O1CCCC1.O1CCOCC1>[Cl:11][C:6]1[N:5]=[C:4]([S:12][CH2:13][CH2:14][CH3:15])[N:3]=[C:2]([NH:23][C@@H:24]2[CH2:28][C@H:27]([OH:29])[CH:26]=[CH:25]2)[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 222689244,6-Dichloro-5-nitro-2-(propylthio)pyrimidineHCID 55281576[1S-cis]-4-amino-2-cyclopenten-1-ol

Product 1

HCID 86757045(1S-cis)-4-[[6-Chloro-5-nitro-2-(propylthio)-pyrimidin-4-yl]amino]-2-cyclopentene-1-olYield 64.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22018518Dioxane tetrahydrofuranSolvent

Procedure

To a solution of 4,6-dichloro-5-nitro-2-propylthiopyrimidine (prepared as described in WO 9703084) (4.00 g) and triethylamine (2.00 ml) in dry tetrahydrofuran (THF) (100 ml) was added a solution of [1S-cis]-4-amino-2-cyclopenten-1-ol (prepared as described by S. F. Martin et al., Tetrahedron Lett., 1992, 33, 3583) (1.48 g) in THF/1,4-dioxane 2:1 (150 ml) dropwise over 1 hour. The reaction mixture was filtered, concentrated and purified (SiO2, ethyl acetate:isohexane 1:4 to 1:1 as eluant) to afford the subtitle compound (3.18 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. custompurified (SiO2, ethyl acetate:isohexane 1:4 to 1:1 as eluant)

Sources & evidence

ORD record
ord-fb8b622378b24374ad174df1ddcb0a0a
Source dataset
uspto-grants-2001_06
Patent number
US06251910B1

Reaction notes

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