Water → HCID 22602788, compound

HRID 2307843Notes

Reaction equation

HRID 2307843 reaction equation
Cl.[NH:2]=[C:3]([NH2:5])[CH3:4].[Cl:6][C:7]1[N:12]=[C:11]([C:13](Cl)(Cl)[S:14]Cl)[CH:10]=[CH:9][N:8]=1.[OH-].[Na+].O>C(Cl)Cl>[Cl:6][C:7]1[N:12]=[C:11]([C:13]2[S:14][N:5]=[C:3]([CH3:4])[N:2]=2)[CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 67170Acetamidine monohydrochlorideHCID 22602785HCID 22602785, compound

Product 1

HCID 22602788HCID 22602788, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

1-Imino-ethanamine hydrochloride (1:1) (0.08 mol) was added at 0° C. to a stirring mixture of intermediate 1 (0.07 mol) in DCM (300 ml). Sodium hydroxide (50%, 20 ml) was added dropwise at 0° C. The mixture was stirred at 5° C. for 1 hour. Water (300 ml) and DCM (300 ml) were added. The mixture was separated into its layers. The aqueous layer was washed twice with DCM. The combined organic layer was dried, filtered and the solvent was evaporated. The residue was purified over silica gel on a glass filter (eluent: DCM). Two pure fractions were collected and their solvents were evaporated, yielding 3.5 g of 2-chloro-4-(3-methyl-1,2,4-thiadiazol-5-yl)pyrimidine (intermediate 2).

Workup

  1. customThe mixture was separated into its layers
  2. washThe aqueous layer was washed twice with DCM
  3. customThe combined organic layer was dried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified over silica gel on a glass
  7. filtrationfilter (eluent: DCM)
  8. customTwo pure fractions were collected
  9. customtheir solvents were evaporated

Sources & evidence

ORD record
ord-db7fc0dae1394368877093d98e9a46d4
Source dataset
uspto-grants-2004_12
Patent number
US06833369B2

Reaction notes

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