Oxalyl chloride → 4-Chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine

HRID 1271027

Reaction equation

HRID 1271027 reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH:7]([N:10]([CH:13]([CH3:15])[CH3:14])[CH:11]=O)([CH3:9])[CH3:8].[NH2:16][C:17]1[N:22]=[C:21](O)[C:20]([I:24])=[CH:19][N:18]=1>ClCCl>[Cl:4][C:21]1[C:20]([I:24])=[CH:19][N:18]=[C:17]([N:16]=[CH:11][N:10]([CH:13]([CH3:15])[CH3:14])[CH:7]([CH3:9])[CH3:8])[N:22]=1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 75912N,N-bis(1-methylethyl)formamideHCID 178508432HCID 178508432, compound

Product 1

HCID 734464514-Chloro-2-diisopropylaminomethyleneamino-5-iodopyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.5 mL of oxalyl chloride in 35 mL of dichloromethane was added dropwise over 25 minutes to an ice water bath-cooled solution of 7.0 mL of N,N-diisopropylformamide in 65 mL of dichloromethane with magnetic stirring. After a few minutes, 4.74 g of 2-amino-4-hydroxy-5-iodopyrimidine was added in one portion. The bath was removed and the solution was stirred at room temperature for 30 minutes, then refluxed for one and one half hours. The solution was cooled and poured into an equal amount of ice-cold saturated aqueous sodium bicarbonate with stirring. The two phases were partitioned and the organic layer washed with additional bicarbonate(2×), water(1×) and finally saturated aqueous brine. After drying over sodium sulfate and filtration, the solution was evaporated in vacuo to yield 10.13 g of a reddish oil. The oil was purified by column chromatography on silica gel, eluting with dichloromethane. Like fractions were pooled, evaporated and triturated with hexanes to give white free flowing crystals, 5.94 g, m.p. 97–100° C.

Workup

  1. waitAfter a few minutes
  2. customThe bath was removed
  3. temperaturerefluxed for one and one half hours
  4. temperatureThe solution was cooled
  5. additionpoured into an equal amount of ice-cold saturated aqueous sodium bicarbonate
  6. stirringwith stirring
  7. customThe two phases were partitioned
  8. washthe organic layer washed with additional bicarbonate(2×), water(1×) and finally saturated aqueous brine
  9. dry with materialAfter drying over sodium sulfate and filtration
  10. customthe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-2f63d07cd13644f8b01ad385cdc396fe
Source dataset
uspto-grants-2007_04
Patent number
US07205297B2

Linked notes

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