Carbon tetrabromide → HCID 178419550, compound

HRID 1600682Notes

Reaction equation

HRID 1600682 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15]O)[CH2:10][CH2:9]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:37]>C(Cl)Cl>[Br:37][CH2:15][CH2:14][C@H:11]1[CH2:12][CH2:13][C@H:8]([NH:7][C:2]2[N:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178520738HCID 178520738, compound

Product 1

HCID 178419550HCID 178419550, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of trans-2-[4-(pyrimidin-2-ylamino)-cyclohexyl]-ethanol (1.51 g, 6.9 mmol) is dissolved in a solution of methylene chloride (25 mL) containing polymer supported triphenylphosphine (2.87 g, approx 8.6 mmol). The mixture is cooled in an ice water bath, and carbon tetrabromide (2.3 g, 7.0 mmol) is added. The reaction is stirred for 1 hour, and the polymeric material was removed by filtration. The filtrate is concentrated and chromatographed on silica gel using a 2:1 mixture of chloroform and ethyl acetate (EtOAc) as the solvent to give trans-[4-(2-Bromoethyl)-cyclohexyl]-pyrimidin-2-yl-amine.

Workup

  1. additioncontaining polymer
  2. temperatureThe mixture is cooled in an ice water bath
  3. customthe polymeric material was removed by filtration
  4. concentrationThe filtrate is concentrated
  5. customchromatographed on silica gel using
  6. additiona 2:1 mixture of chloroform and ethyl acetate (EtOAc) as the solvent

Sources & evidence

ORD record
ord-77520aca04e94639a9bce59f01065dd3
Source dataset
uspto-grants-1999_11
Patent number
US05977110

Reaction notes

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