Trifluoroacetic acid → HCID 23446450, compound

HRID 1841612Notes

Reaction equation

HRID 1841612 reaction equation
C(OC(=O)[NH:7][C:8]1[N:13]=[CH:12][C:11]([C:14]#[C:15][CH2:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[CH:10][N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:21][N:19]([CH3:20])[CH2:18][CH2:17][CH2:16][C:15]#[C:14][C:11]1[CH:10]=[N:9][C:8]([NH2:7])=[N:13][CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68614618HCID 68614618, compound

Product 1

HCID 23446450HCID 23446450, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.47 g (3.2 mmol) of [5-(5-Dimethylamino-pent-1-ynyl)-pyrimidin-2-yl]-carbamic acid tert-butyl ester in 16 ml CH2Cl2 was treated at 0° C. with 8 ml TFA (during 20 min). The solution was warmed up to room temperature during 1 h, concentrated and the residual oil was extracted with aqueous sat. NaHCO3 (+Na2CO3)(3×)/CH2Cl2(3×). The organic phases were washed with aqueous 10% NaCl solution, dried (Na2SO4) and evaporated to yield 0.62 g (95%) of 5-(5-Dimethylamino-pent-1-ynyl)-pyrimidin-2-ylamine, mp: 126-127° C.; MS: 205 (MH+).

Workup

  1. concentrationconcentrated
  2. extractionthe residual oil was extracted with aqueous sat. NaHCO3 (+Na2CO3)(3×)/CH2Cl2(3×)
  3. washThe organic phases were washed with aqueous 10% NaCl solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-427610d2aec0400e9af5f9b69a047220
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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