Ammonium Hydroxide → HCID 12971789, compound

HRID 2227788Notes

Reaction equation

HRID 2227788 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[NH:12][C:13](=O)[C:14]3[NH:15][CH:16]=[N:17][C:18]=3[N:19]=2)=[CH:6][N:5]=1)[CH3:2].S(Cl)([Cl:23])=O.C(=O)(O)[O-].[Na+].[OH-].[NH4+]>O.CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:19]=[C:18]3[C:14]([NH:15][CH:16]=[N:17]3)=[C:13]([Cl:23])[N:12]=2)=[CH:6][N:5]=1)[CH3:2]

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 516892Sodium Bicarbonate2×HCID 136023931HCID 136023931, compound

Product 1

HCID 12971789HCID 12971789, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of N2-(2-Ethoxypyridin-5-yl)guanine (6.35 g; 23.3 mmol) and N,N-dimethylformamide (70 mL) is cooled to 0° C. and treated dropwise with thionyl chloride (5.6 mL; 76.8 mmol). An additional 15 ml of N,N-dimethylformamide is added and the mixture is heated at 50° C. for 1 h. The reaction mixture is cooled to room temperature and poured slowly into a solution of sodium bicarbonate (8 g) in water (80 mL). The pH is adjusted to 6 with saturated aqueous sodium bicarbonate solution and the mixture is chilled overnight. The precipitate is collected by filtration and washed with water and methanol to give a brown solid which is dissolved in warm concentrated ammonium hydroxide (30 mL) and allowed to stand at room temperature for 3 days. The precipitate is collected by filtration and washed with water and methanol to afford 2-[(2-Ethoxypyrid-5-yl)amino]-6-chloropurine (4.72 g).

Workup

  1. temperaturethe mixture is heated at 50° C. for 1 h
  2. temperatureThe reaction mixture is cooled to room temperature
  3. temperaturethe mixture is chilled overnight
  4. filtrationThe precipitate is collected by filtration
  5. washwashed with water and methanol
  6. customto give a brown solid which
  7. dissolutionis dissolved
  8. filtrationThe precipitate is collected by filtration
  9. washwashed with water and methanol

Sources & evidence

ORD record
ord-82c1959f3ce34b7d82693a4568a07616
Source dataset
uspto-grants-2002_07
Patent number
US06414147B1

Reaction notes

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