1,1-dimethylethyl (2S)-2-({[2-chloro-5-(dihydroxyamino)-4-pyrimidinyl]amino}methyl)-1-pyrrolidinecarboxylate → 1,1-dimethylethyl (2S)-2-{[(5-amino-4-pyrimidinyl)amino]methyl}-1-pyrrolidinecarboxylate

HRID 1366709Notes

Reaction equation

HRID 1366709 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:5]([N:22](O)O)=[CH:4][N:3]=1>CO>[NH2:22][C:5]1[C:6]([NH:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[N:7][CH:2]=[N:3][CH:4]=1

Participants

3

Reactant 1

HCID 866370351,1-dimethylethyl (2S)-2-({[2-chloro-5-(dihydroxyamino)-4-pyrimidinyl]amino}methyl)-1-pyrrolidinecarboxylate

Product 1

HCID 669363271,1-dimethylethyl (2S)-2-{[(5-amino-4-pyrimidinyl)amino]methyl}-1-pyrrolidinecarboxylateYield 94.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,1-Dimethylethyl (2S)-2-({[2-chloro-5-(dihydroxyamino)-4-pyrimidinyl]amino}methyl)-1-pyrrolidinecarboxylate (2.064 g, 5.74 mmol) was dissolved in MeOH (40 mL), degassed and placed under argon. 10% Pd/C (619 mg) was added, and the contents were thoroughly degassed and placed under a hydrogen balloon for 2 h. The contents were then degassed, and the Pd/C was removed by filtration through a fiberglass filter, washing with MeOH. The filtrate was concentrated in vacuo to provide pure 1,1-dimethylethyl (2S)-2-{[(5-amino-4-pyrimidinyl)amino]methyl}-1-pyrrolidinecarboxylate (1.589 g, 94%). LCMS: (M+H)+: 294.1.

Workup

  1. customdegassed
  2. addition10% Pd/C (619 mg) was added
  3. customthe contents were thoroughly degassed
  4. customfor 2 h
  5. customThe contents were then degassed
  6. customthe Pd/C was removed by filtration through a fiberglass
  7. filtrationfilter
  8. washwashing with MeOH
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-87e1d2e0e6a54d829eaa14894787b1f7
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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