Hydrochloric Acid → HCID 22841379, compound

HRID 2292238Notes

Reaction equation

HRID 2292238 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.[H-].[Na+].C=O.Cl.[CH2:24]([O:31][C@@H:32]([CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:33][O:34][CH2:35]Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:35][O:34][CH2:33][C@@H:32]([O:31][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:37][O:38][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[C:4]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 24758Sodium hydride2×HCID 116518242-chloro-6-phenylmethyloxy-1H-purineHCID 14652419HCID 14652419, compound

Product 1

HCID 22841379HCID 22841379, compoundYield 571%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-6-benzyloxypurine (782 mg, 3 mmol) was dissolved in sieve-dried DMF (10 ml) and 60% NaH in oil (160 mg; 4 mmol of NaH) was added. This mixture was strired under N2 for 20 minutes and then 963 mg (3 mmol) of (S)-2,3-dibenzyl-oxy-1-chloromethoxy propane (prepared from 1,2-di-O-benzyl-D-glycerol by chloromethylation with formaldehyde and HCl in methylene chloride at 0° C. using the method disclosed in European Patent Application No. 82401571.3, publication No. 0 074 306, or U.S. Ser. No. 617,868, filed June 6, 1984 in 10 ml of dry DMF was added. This mixture was stirred at room temperature under N2 overnight after which time an additional 100 mg of (S)-2,3-dibenzyloxy-1-chloromethoxypropane was added. After 3 hours, the reaction was evaporated to dryness in vacuo, followed by an additional evaporation from toluene. The crude product was chromatographed on a column of Baker 3405 silica gel, developed first with ethyl ether and then with ethyl acetate. Fractions containing the required product were pooled and evaporated to dryness to give 970 mg (1.78 mmol, 59% yield) of pure material. 500 mg (0.92 mmol, 30.1% yield) of suspected N7 - isomer (NMR and mass spectroscopic identification) was obtained from later fractions, readily separated from the N9 isomer.

Workup

  1. additionwas added
  2. additionwas added
  3. waitAfter 3 hours
  4. customthe reaction was evaporated to dryness in vacuo
  5. customfollowed by an additional evaporation from toluene
  6. customThe crude product was chromatographed on a column of Baker 3405 silica gel
  7. additionFractions containing the required product
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-561df0a856f44f748c1a0f553909875c
Source dataset
uspto-grants-1989_01
Patent number
US04801710

Reaction notes

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