1,3-Dibromopropane → HCID 178506373, compound

HRID 1819427Notes

Reaction equation

HRID 1819427 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([Cl:16])=[CH:14][N:13]=[C:12]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][C:26]([F:29])([F:28])[F:27])[N:11]=2)[CH2:4][CH2:3]1.Br[CH2:31][CH2:32][CH2:33]Br>CC(N(C)C)=O>[N:1]1([C@H:2]2[CH2:3][CH2:4][C@H:5]([CH2:8][NH:9][C:10]3[C:15]([Cl:16])=[CH:14][N:13]=[C:12]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][C:26]([F:27])([F:28])[F:29])[N:11]=3)[CH2:6][CH2:7]2)[CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 80011,3-DibromopropaneHCID 178511542HCID 178511542, compound

Product 1

HCID 178506373HCID 178506373, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

N4-[(trans-4-aminocyclohexyl)methyl]-5-chloro-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine (178 mg, 0.41 mmol) was dissolved in DMA (5 mL). To this solution was added 1,3-dibromopropane (208 μL, 2.01 mmol) and NaCO3 (217 mg, 2.01 mmol). The reaction was heated in the microwave at 100° C. for 5 min. The volatiles were removed and the reaction was diluted with EtOAc and poured into H2O. The aqueous phase was separated and extracted two more times with EtOAc. The organic layers were combined, dried (Na2SO4), decanted and concentrated. The crude product was purified on a 2000 micron SiO2 preparative TLC plate, eluting with 10:1 CH2Cl2:MeOH (1% NH4OH) to afford 102 mg (53%) of the title compound, m/z 470.5 [M+1]+.

Workup

  1. customThe volatiles were removed
  2. additionthe reaction was diluted with EtOAc
  3. additionpoured into H2O
  4. customThe aqueous phase was separated
  5. extractionextracted two more times with EtOAc
  6. dry with materialdried (Na2SO4)
  7. customdecanted
  8. concentrationconcentrated
  9. customThe crude product was purified on a 2000 micron SiO2 preparative TLC plate
  10. washeluting with 10:1 CH2Cl2

Sources & evidence

ORD record
ord-ea9f3d782bf3415e9e83716562f91926
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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