Triethylamine → 6-[N-(2-Chloroethyl)carbamoyl]oxypurine

HRID 2413890Notes

Reaction equation

HRID 2413890 reaction equation
[NH:1]1[C:9](=[O:10])[C:8]2[NH:7][CH:6]=[N:5][C:4]=2[N:3]=[CH:2]1.C(N(CC)CC)C.[Cl:18][CH2:19][CH2:20][N:21]=[C:22]=[O:23]>CN(C)C=O>[Cl:18][CH2:19][CH2:20][NH:21][C:22]([O:10][C:9]1[N:1]=[CH:2][N:3]=[C:4]2[C:8]=1[NH:7][CH:6]=[N:5]2)=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 135398638Hypoxanthine

Product 1

HCID 142548556-[N-(2-Chloroethyl)carbamoyl]oxypurine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of hypoxanthine (6.8 g, 50 mmoles) in dimethylformamide (200 ml) there is added triethylamine (5.05 g, 50 mmoles) and then at 15° to 20° C., 2-chloroethylisocyanate (5.8 g, 55 mmoles is dripped in. The reaction mixture is stirred at this temperature until dissolution of the solid (approx. for 2 hours), thereafter poured into an ice-water mixture (750 ml), the precipitate of the title product is separated by suction, washed with acetone and dried at room temperature. The yield is 8.2 g (67.8%) of compound Ib, m.p. 320°-240° C. (with decomposition), UV absorption spectrum (in dimethylsulfoxide), λ max 275 nm (log ⃝3.76).

Workup

  1. customat 15° to 20° C.
  2. customthe precipitate of the title product is separated by suction
  3. washwashed with acetone
  4. customdried at room temperature
  5. customThe yield is 8.2 g (67.8%) of compound Ib, m.p. 320°-240° C. (with decomposition), UV absorption spectrum (in dimethylsulfoxide), λ max 275 nm (log ⃝3.76)

Sources & evidence

ORD record
ord-4af0d7b3813b42a7bbca0b62c3c5a937
Source dataset
uspto-grants-1988_01
Patent number
US04720497

Reaction notes

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