Diisopropylethylamine → HCID 89422526, compound

HRID 1752438Notes

Reaction equation

HRID 1752438 reaction equation
Cl.[NH:2]1[CH2:6][C@H:5]([OH:7])[C@@H:4]([OH:8])[CH2:3]1.[Cl:9][C:10]1[N:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[C:12](Cl)[N:11]=1.CCN(C(C)C)C(C)C>C(#N)C>[Cl:9][C:10]1[N:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[C:12]([N:2]2[CH2:6][C@H:5]([OH:7])[C@@H:4]([OH:8])[CH2:3]2)[N:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 66787043276862-76-1

Product 1

HCID 89422526HCID 89422526, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of the (3S,4S)-pyrrolidine-3,4-diol hydrochloride (0.773 g, 5.54 mmol), methyl 2,6-dichloropyrimidine-4-carboxylate (1.038 g, 5.01 mmol), and iPr2NEt (2.00 mL, 11.5 mmol) in acetonitrile (25 mL) was heated at 50° C. for 3 h. The reaction mixture was evaporated in vacuo and the residue chromatographed over silica gel with 25-75% acetone in hexanes. The product fractions were evaporated in vacuo to give methyl 2-chloro-6-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)pyrimidine-4-carboxylate as a light tan powder (1.132 g, 4.14 mmol, 83% yield). LC/MS: m/z=274.2 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue chromatographed over silica gel with 25-75% acetone in hexanes
  3. customThe product fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-9de4d7de328643aa8193e6884dd76113
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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