Trifluoroacetic acid → (S)-5-methyl-4-(3-methylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1892118Notes

Reaction equation

HRID 1892118 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]2[C:9]3[C:16]([CH3:17])=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:5][CH2:4][N:3]1C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl>[CH3:17][C:16]1[C:9]2[C:8]([N:6]3[CH2:5][CH2:4][NH:3][C@@H:2]([CH3:1])[CH2:7]3)=[N:13][CH:12]=[N:11][C:10]=2[NH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68796427(S)-tert-butyl 2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboxylate

Product 1

HCID 68958720(S)-5-methyl-4-(3-methylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidineYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The Boc-protected piperazine from step A (1.5 g, 4.5 mmol) was added to a 1:1 mixture of trifluoroacetic acid and dichloromethane (10 ml). The reaction was stirred overnight, then concentrated under vacuum, diluted with dichloromethane, and neutralized with sat. aq. sodium bicarbonate. The layers were separated, and the aqueous layer was back extracted with more dichloromethane. The combined organic fractions were dried over MgSO4 and concentrated under vacuum to give (S)-5-methyl-4-(3-methylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine (0.80 g, 3.5 mmol, 76%).

Workup

  1. concentrationconcentrated under vacuum
  2. additiondiluted with dichloromethane
  3. customThe layers were separated
  4. extractionthe aqueous layer was back extracted with more dichloromethane
  5. dry with materialThe combined organic fractions were dried over MgSO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e36d704d8e354be9bd0dda4125206f7f
Source dataset
uspto-grants-2013_08
Patent number
US08507672B2

Reaction notes

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