Sodium Carbonate → HCID 21259081, compound

HRID 481743Notes

Reaction equation

HRID 481743 reaction equation
NC1N=C2C(NC=N2)=C(Cl)N=1.[CH:12]([NH:14][C:15]1[N:23]=[C:22]2[C:18]([NH:19][CH:20]=[N:21]2)=[C:17]([Cl:24])[N:16]=1)=[O:13].P(Cl)(Cl)(Cl)=O.N1[C:39](=[O:40])[C:38]2NC=NC=2N=C1N.C(=O)([O-])[O-].[Na+].[Na+]>O.ClCCCl.CN(C)C=O>[C:39]([OH:40])(=[O:13])[CH3:38].[CH:12]([NH:14][C:15]1[N:23]=[C:22]2[C:18]([NH:19][CH:20]=[N:21]2)=[C:17]([Cl:24])[N:16]=1)=[O:13]

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 53603492-Amino-6-chloropurine2×HCID 109283082-formylamino-6-chloropurineHCID 135398634Guanine

Product 1

HCID 21259081HCID 21259081, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The 2-amino-6-chloropurine having an acicular or irregular-shaped crystal form can be prepared by hydrolyzing 2-formylamino-6-chloropurine or a salt thereof in water in the presence of an acid or an alkali, followed by neutralizing the resulting reaction mixture. For example, the 2-amino-6-chloropurine having an acicular or irregular-shaped crystal form can be produced by a conventional method as disclosed in JP-6-157530. Specifically, dimethylformamide, phosphorus oxychloride and guanine are added to 1,2-dichloroethane, and the mixture is stirred with heating. After cooling, the reaction mixture is added to water, to which sodium carbonate is added to adjust the pH of the mixture to 4. Then, the aqueous layer is separated therefrom, which is then neutralized by adding sodium hydroxide thereto. The precipitated crystal of 2-dimethylaminomethyleneamino-6-chloropurine is filtered off and added to an aqueous solution of acetic acid. The solution is stirred with heating to precipitate crystals. The precipitated crystals are filtered off and washed with water to give crystals of 2-formylamino-6-chloropurine acetate. The crystals of 2-formylamino-6-chloropurine acetate are then dissolved in an aqueous solution of a metal hydroxide such as sodium hydroxide with stirring. The solution is neutralized with hydrochloric acid, acetic acid or sulfuric acid to precipitate crystals. The precipitated crystals are filtered off to obtain acicular or irregular-shaped white crystals of 2-amino-6-chloropurine.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewith heating
  3. temperatureAfter cooling
  4. additionis added
  5. customThen, the aqueous layer is separated
  6. additionby adding sodium hydroxide
  7. filtrationThe precipitated crystal of 2-dimethylaminomethyleneamino-6-chloropurine is filtered off
  8. additionadded to an aqueous solution of acetic acid
  9. stirringThe solution is stirred
  10. temperaturewith heating
  11. customto precipitate crystals
  12. filtrationThe precipitated crystals are filtered off
  13. washwashed with water

Sources & evidence

ORD record
ord-d9821f35d5db40d088d4a9872e040147
Source dataset
uspto-grants-1998_08
Patent number
US05789590

Reaction notes

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