2-[4-(Propan-2-yl)piperidin-1-yl]ethan-1-amine → 9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-N-[2-(4-isopropyl-1-piperidinyl)ethyl]-9H-purine-2-carboxamide

HRID 2184258Notes

Reaction equation

HRID 2184258 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([C:34](OC)=[O:35])=[N:14][C:15]=2[NH:19][CH2:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH:38]([CH:41]1[CH2:46][CH2:45][N:44]([CH2:47][CH2:48][NH2:49])[CH2:43][CH2:42]1)([CH3:40])[CH3:39]>C(OCC)C>[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([C:34]([NH:49][CH2:48][CH2:47][N:44]1[CH2:45][CH2:46][CH:41]([CH:38]([CH3:40])[CH3:39])[CH2:42][CH2:43]1)=[O:35])=[N:14][C:15]=2[NH:19][CH2:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 219783132-[4-(Propan-2-yl)piperidin-1-yl]ethan-1-amineHCID 56614351Methyl 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate

Product 1

HCID 101896619-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-N-[2-(4-isopropyl-1-piperidinyl)ethyl]-9H-purine-2-carboxamideYield 50.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 18) (92 mg, 0.18 mmol) and 2-(4-isopropyl-1-piperidinyl)ethylamine (Preparation 20) (100 mg, 0.6 mmol) was heated at 120° C. under a nitrogen atmosphere for 75 minutes. The reaction mixture was allowed to cool to room temperature and diethyl ether (2 ml) added to precipitate a crude product. The solvent was decanted off the gum which was then triturated with ethyl acetate (2 ml). The resulting white solid was filtered off and dried to give the title compound (59 mg).

Workup

  1. temperatureto cool to room temperature
  2. customto precipitate a crude product
  3. customThe solvent was decanted off the gum which
  4. customwas then triturated with ethyl acetate (2 ml)
  5. filtrationThe resulting white solid was filtered off
  6. customdried

Sources & evidence

ORD record
ord-fbd9e7793137499cb59ce4f6de1c554d
Source dataset
uspto-grants-2005_05
Patent number
US06900309B1

Reaction notes

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