Sodium Nitrite → 1,1-dimethylethyl (2S)-2-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-1-pyrrolidinecarboxylate

HRID 1366710Notes

Reaction equation

HRID 1366710 reaction equation
[NH2:1][C:2]1[C:3]([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:4][CH:5]=[N:6][CH:7]=1.[N:22]([O-])=O.[Na+]>C(O)(=O)C.O>[N:1]1[C:2]2[CH:7]=[N:6][CH:5]=[N:4][C:3]=2[N: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:22]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 669363271,1-dimethylethyl (2S)-2-{[(5-amino-4-pyrimidinyl)amino]methyl}-1-pyrrolidinecarboxylate

Product 1

HCID 669363511,1-dimethylethyl (2S)-2-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-1-pyrrolidinecarboxylateYield 114.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1,1-Dimethylethyl (2S)-2-{[(5-amino-4-pyrimidinyl)amino]methyl}-1-pyrrolidinecarboxylate (1.6633 g, 5.67 mmol) and sodium nitrite (469 mg, 6.80 mmol) were dissolved in a mixture of acetic acid (5 mL) and water (8 mL), and the mixture was stirred vigorously for 1 h. The solution was concentrated in vacuo to provide 1,1-dimethylethyl (2S)-2-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-1-pyrrolidinecarboxylate (1.98 g, >99%). LCMS: (M+H)+: 305.2.

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-205a89b72cd84e8aa7a6dbefe78ef466
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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