Water → 7H-Pyrrolo[2,3-d]pyriMidin-4-aMine, N-Methyl-N-[(3R,4R)-4-Methyl-1-(phenylMethyl)-3-piperidinyl]-7-[(4-Met hylphenyl)sulfonyl]-

HRID 1517982Notes

Reaction equation

HRID 1517982 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1.C1(C)C=CC(C([C@@](C(O)=O)(O)[C@@](C(C2C=CC(C)=CC=2)=O)(O)C(O)=O)=O)=CC=1.[CH2:49]([N:56]1[CH2:61][CH2:60][C@@H:59]([CH3:62])[C@@H:58]([NH:63][CH3:64])[CH2:57]1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH2:49]([N:56]1[CH2:61][CH2:60][C@@H:59]([CH3:62])[C@@H:58]([N:63]([CH3:64])[C:2]2[C:3]3[CH:10]=[CH:9][N:8]([S:11]([C:14]4[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=4)(=[O:13])=[O:12])[C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:57]1)[C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 442289674-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidineHCID 131729858HCID 131729858, compound

Product 1

HCID 159846807H-Pyrrolo[2,3-d]pyriMidin-4-aMine, N-Methyl-N-[(3R,4R)-4-Methyl-1-(phenylMethyl)-3-piperidinyl]-7-[(4-Met hylphenyl)sulfonyl]-Yield 163.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a clean, dry, nitrogen-purged reactor were charged 4-chloro-7-(4-methyl-benzenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (25.12 g, 0.082 mol), bis-(3R,4R)-(1-benzyl-4-methyl-piperidine-3-yl)-methylamine di-p-toluoyl-L-tartaric acid (40.31 g, 0.041 mol), potassium carbonate (34.2 g, 0.245 mol), and water (125.6 ml). The mixture was heated to 95-105° C. for a minimum of 10 hours, then cooled to 45-55° C. Acetonitrile (25 ml) was charged and the slurry was held at 45-55° C. for a minimum of 1 hour. The mixture was further cooled to 20-30° C. and stirred for a minimum of 5 hours. The resulting solids were isolated by filtration and washed with water (50 ml). After drying, 32.8 g (82.1%) of the title compound were isolated.

Workup

  1. customTo a clean, dry
  2. customnitrogen-purged reactor
  3. temperaturecooled to 45-55° C
  4. customwas held at 45-55° C. for a minimum of 1 hour
  5. temperatureThe mixture was further cooled to 20-30° C.
  6. customThe resulting solids were isolated by filtration
  7. washwashed with water (50 ml)
  8. customAfter drying

Sources & evidence

ORD record
ord-dd30d70e0ce74440a4c9641cb8c13445
Source dataset
uspto-grants-2012_07
Patent number
US08232394B2

Reaction notes

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