Ammonia → (2R,3R,4R,5R)-2-(2,4-diaminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol

HRID 1836268Notes

Reaction equation

HRID 1836268 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:6]=2[N:7]=1.[NH3:22]>>[NH2:1][C:2]1[N:3]=[C:4]([NH2:22])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 11483860(2R,3R,4R,5R)-2-(2-amino-4-chloropyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol

Product 1

HCID 3011904(2R,3R,4R,5R)-2-(2,4-diaminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol

Procedure

A mixture of the product from Step B of Example 118 (24 mg) in aqueous ammonia (30%, 10 mL) was heated in a stainless steel autoclave at 100° C. overnight, then cooled and evaporated. The residue was purified on a silica gel column with CH2Cl2/MeOH (10/1 and 5/1) as the eluent to afford the title compound (15 mg).

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe residue was purified on a silica gel column with CH2Cl2/MeOH (10/1 and 5/1) as the eluent

Sources & evidence

ORD record
ord-c1fe2da97c9e4ab6bd3c470bb9697f9d
Source dataset
uspto-grants-2004_08
Patent number
US06777395B2

Reaction notes

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