Cyclopropylamine → (2R,3R,4R,5R)-2-[2-amino-4-(cyclopropylamino)pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)-3-methyloxolane-3,4-diol

HRID 1836243Notes

Reaction equation

HRID 1836243 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.[CH:22]1([NH2:25])[CH2:24][CH2:23]1>>[NH2:1][C:2]1[N:3]=[C:4]([NH:25][CH:22]2[CH2:24][CH2:23]2)[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 69828CyclopropylamineHCID 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 9858930(2R,3R,4R,5R)-2-[2-amino-4-(cyclopropylamino)pyrrolo[2,3-d]pyrimidin-7-yl]-5-(hydroxymethyl)-3-methyloxolane-3,4-diol

Procedure

A solution of 2-amino-4-chloro-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (Example 118, Step B) (21 mg, 0.07 mmol) in cyclopropylamine (0.5 mL) was heated at 70° C. for two days, then evaporated to an oily residue and purified on a silica gel column with CH2Cl2/MeOH, 20/1, as eluent to give the title compound as a white solid (17 mg).

Workup

  1. customevaporated to an oily residue
  2. custompurified on a silica gel column with CH2Cl2/MeOH, 20/1, as eluent

Sources & evidence

ORD record
ord-1b3a31fce57347ec8fb1a78d6561a30f
Source dataset
uspto-grants-2004_08
Patent number
US06777395B2

Reaction notes

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