Nitric Acid → 5-nitro-7H-pyrrolo[2,3-d]pyrimidine

HRID 1775146Notes

Reaction equation

HRID 1775146 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[CH:4]=[N:3][CH:2]=1.[N+:10]([O-])([OH:12])=[O:11].C(=O)(O)[O-].[Na+]>O>[N+:10]([C:9]1[C:5]2[CH:4]=[N:3][CH:2]=[N:1][C:6]=2[NH:7][CH:8]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 2615917H-Pyrrolo(2,3-d)pyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 579631485-nitro-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

5-Nitro-7H-pyrrolo[2,3-d]pyrimidine (8) is prepared by adding 7H-pyrrolo[2,3-d]pyrimidine (6) to fuming nitric acid while cooling (e.g. 0° C.). After stirring for one to several hours, water is carefully added and the mixture neutralized with saturated sodium bicarbonate. The solids are collected by filtration and dried to provide 5-nitro-7H-pyrrolo[2,3-d]pyrimidine 8.

Workup

  1. custom5-Nitro-7H-pyrrolo[2,3-d]pyrimidine (8) is prepared
  2. additionis carefully added
  3. filtrationThe solids are collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-605c5fd85d2743878f39e8d35b17e094
Source dataset
uspto-grants-2016_02
Patent number
US09260437B2

Reaction notes

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