1-Bromo-3-chloropropane → HCID 66673908, compound

HRID 219697Notes

Reaction equation

HRID 219697 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:8]=[C:7]([C:17]2([CH3:20])[CH2:19][CH2:18]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][CH2:36][CH2:37][Cl:38]>CN(C)C=O>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:12][CH2:13][N:14]([CH2:35][CH2:36][CH2:37][Cl:38])[CH2:15][CH2:16]2)[CH:8]=[C:7]([C:17]2([CH3:20])[CH2:19][CH2:18]2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 690260782-tert-Butyl-4-(1-methylcyclopropyl)-6-(piperazin-1-yl)pyrimidine

Product 1

HCID 66673908HCID 66673908, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

7 g of 2-tert-butyl-4-piperazin-1-yl-6-(1-methylcyclopropyl)-pyrimidine (25.5 mmol; prepared by analogy to steps a.2.1 to a.2.4 starting from 1-methylcyclopropyl carbonic acid chloride) were dissolved in 50 ml of dimethyl formamide. 2.58 of triethylamine (25.5 mmol), and 3.53 g of potassium carbonate were added, followed by dropwise addition of 4.62 g of 1-bromo-3-chloropropane. After stirring for 1.5 h at 50° C. the reaction mixture was stirred overnight at room temperature. The precipitate was filtered off and washed with dimethylformamide. The filtrate was partitioned between 150 ml of ethyl acetate and 50 ml of water. The organic layer was separated and the aqueous layer was extracted with 30 ml of ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified by chromatography on silica gel (ethyl acetate) to yield 4.6 g of the title compound.

Workup

  1. stirringwas stirred overnight at room temperature
  2. filtrationThe precipitate was filtered off
  3. washwashed with dimethylformamide
  4. customThe filtrate was partitioned between 150 ml of ethyl acetate and 50 ml of water
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with 30 ml of ethyl acetate
  7. dry with materialThe combined organic layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was purified by chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-a6aa3edafc8741bd8a30c29d258e749b
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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