Hydrochloric Acid → 9-Benzyl-2,6-dichloro-9H-purine

HRID 1277622Notes

Reaction equation

HRID 1277622 reaction equation
[CH2:1]([N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][C:11]([Cl:18])=[N:12][C:13]=2N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:19].C(N1C=NC2C1=NC(OCCC)=NC=2N)C1C=CC=CC=1>C(O)CC>[CH2:1]([N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][C:11]([Cl:18])=[N:12][C:13]=2[Cl:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2764829-Benzyl-2-chloro-9h-purin-6-amineHCID 12898912HCID 12898912, compound

Product 1

HCID 2366419-Benzyl-2,6-dichloro-9H-purine

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Procedure

A mixture of 9-benzyl-2-chloro-9H-adenine (130 mg., 0.5 mmole) and 1.25 ml. of 1 N sodium n-propoxide in n-propanol in 13 ml. of n-propanol is refluxed overnight, neutralized with hydrochloric acid and evaporated in vacuo. Trituration of residual material with water provides 118 mg. of crude product which crystallized from aqueous ethanol affords 90 mg. (64%) of analytically pure 9-benzyl-2-n-propoxy-9H-adenine, m.p. 178°-180° C. (dec.). IR(KBr): 3280, 3130, 2970, 1660, 1595, 1405, 1350, 1330, 1275 cm-1. UV:λmaxEtOH 254 nm(ε8,800), 269.5 nm(ε12,800). NMR(CDCl3):δ1.02(3H,t,J=7 Hz), 1.6-2.1(2H,m), 4.25(2H,t,J=7 Hz), 5.20(2H,s), 6.00(2H,br.s), 7.23(5H,m), 7.50(1H,s).

Workup

  1. customevaporated in vacuo
  2. customTrituration of residual material with water provides 118 mg
  3. customof crude product which crystallized from aqueous ethanol
  4. customaffords 90 mg

Sources & evidence

ORD record
ord-0da8d674afc84d67a470581e3add3467
Source dataset
uspto-grants-1981_07
Patent number
US04278675

Reaction notes

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