1,4-Dibromobutane → HCID 178505999, compound

HRID 1819428Notes

Reaction equation

HRID 1819428 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([F: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][CH2:34]Br>CC(N(C)C)=O>[F:16][C:15]1[C:10]([NH:9][CH2:8][C@H:5]2[CH2:4][CH2:3][C@H:2]([N:1]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH2:7][CH2:6]2)=[N:11][C:12]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][C:26]([F:27])([F:28])[F:29])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 80561,4-DibromobutaneHCID 178511543HCID 178511543, compound

Product 1

HCID 178505999HCID 178505999, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

N4-[(trans-4-aminocyclohexyl)methyl]-5-fluoro-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine (71 mg, 0.17 mmol) was dissolved in DMA (2 mL). To this solution was added 1,4-dibromobutane (81 μL, 0.68 mmol) and NaCO3 (72 mg, 0.68 mmol). The reaction was heated in the microwave at 100° C. for 20 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 by twice running on a 1000 micron SiO2 Prep TLC plate, eluting with 10:1 CH2Cl2:MeOH (1% NH4OH) to afford 36 mg (45%) of the title compound, m/z 468.6 [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
  10. washeluting with 10:1 CH2Cl2

Sources & evidence

ORD record
ord-27536449fdcc424d883e450ac0011e42
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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