Diisopropylethylamine → Methyl [(6-chloro-5-formylpyrimidin-4-yl)thio]acetate

HRID 32514

Reaction equation

HRID 32514 reaction equation
[CH3:1]CN(C(C)C)C(C)C.[Cl:10][C:11]1[C:16]([CH:17]=[O:18])=[C:15](Cl)[N:14]=[CH:13][N:12]=1.C[CH:21]([SH:25])[C:22]([O-:24])=[O:23]>C(Cl)Cl>[Cl:10][C:11]1[N:12]=[CH:13][N:14]=[C:15]([S:25][CH2:21][C:22]([O:24][CH3:1])=[O:23])[C:16]=1[CH:17]=[O:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde2×HCID 156077362-Mercaptopropionate

Product 1

HCID 66367174Methyl [(6-chloro-5-formylpyrimidin-4-yl)thio]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

DIPEA (4.1 mL) was added to a solution of 4,6-dichloropyrimidine-5-carbaldehyde (intermediate 8) (4.2 g) in DCM (85 mL) under an inert atmosphere. The solution was cooled to −10° C. and methylthioglycolate (2.1 mL) in DCM (40 mL) was added dropwise over 30 minutes. The reaction mixture was allowed to warm to ambient temperature over 2 hours, washed with water (4×50 mL), dried (MgSO4), filtered and concentrated in vacuo to give the title compound as an orange oil which later solidified (5.4 g, 92%);

Workup

  1. temperatureto warm to ambient temperature over 2 hours
  2. washwashed with water (4×50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c09aeddcea34b0387908df9b7e63a0a
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Linked notes

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