HCID 12012064, compound → 280138-71-8

HRID 2118091Notes

Reaction equation

HRID 2118091 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][O:14][C@@H:13]([CH2:16][O:17]C(=O)C3C=CC=CC=3)[O:12]2)=[C:4]([NH:26][CH:27]2[CH2:29][CH2:28]2)[N:3]=1>N.CO>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][O:14][C@@H:13]([CH2:16][OH:17])[O:12]2)=[C:4]([NH:26][CH:27]2[CH2:28][CH2:29]2)[N:3]=1

Participants

3

Reactant 1

HCID 12012064HCID 12012064, compound

Product 1

HCID 485995280138-71-8Yield 41%

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

Benzoic acid 4(R)-(2-amino-6-cyclopropylamino-purin-9-yl)-[1,3]dioxolan-2(R)-ylmethyl ester crude (1304 g) was stirred with NH3/MeOH (20 L, 2M) for 20 hours at room temperature. Excess ammonia was removed by sparging nitrogen gas through the reaction mixture. The volatiles were removed in vacuo to give a black syrup which was further purified by column chromatography (MeOH/DCM:25/1) to give crude final product (910 g). The crude product was crystallized from ethyl acetate/ethanol to give [4(R)-(2-Amino-6-cyclopropylamino-purin-9-yl)-[1,3]dioxolan-2(R)-yl]-methanol (455 g, 41% yield from acetoxy-sugar).

Workup

  1. customExcess ammonia was removed
  2. customby sparging nitrogen gas through the reaction mixture
  3. customThe volatiles were removed in vacuo
  4. customto give a black syrup which
  5. customwas further purified by column chromatography (MeOH/DCM:25/1)
  6. customto give crude final product (910 g)
  7. customThe crude product was crystallized from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-b0252c789b264fb1bd5a6fad44d8bb73
Source dataset
uspto-grants-2008_10
Patent number
US07442813B2

Reaction notes

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