HCID 53908910, compound → HCID 67268602, compound

HRID 251499Notes

Reaction equation

HRID 251499 reaction equation
[C:1]1([Mg]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:9][C:10]1[C:11]2[C:18]([C:19]3[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=3)=[CH:17][N:16]([CH:27]([CH3:29])[CH3:28])[C:12]=2[N:13]=[CH:14][N:15]=1>C1COCC1.C1(C)C=CC=CC=1.C1COCC1>[NH2:9][C:10]1[C:11]2[C:18]([C:19]3[CH:20]=[CH:21][C:22]([CH:23]([OH:24])[C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:25][CH:26]=3)=[CH:17][N:16]([CH:27]([CH3:29])[CH3:28])[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

5

Reactant 2

HCID 53908910HCID 53908910, compoundHCID 178478979HCID 178478979, compound

Product 1

HCID 67268602HCID 67268602, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Conditions

Temperature
0 °C

Procedure

Phenylmagnesium chloride (1.5 ml of a 2M solution in THF) was added dropwise with stirring under nitrogen to a solution of 4-(4-amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzaldehyde (0.25 g) in toluene/THF (1:1, 16 ml) at minus 78° C. under nitrogen. After the addition the mixture was allowed to warm 0° C. and maintained at this temperature for 40 minutes. The reaction was quenched by the dropwise addition of saturated ammonial chloride solution (4 ml) at 0° C. The mixture was allowed to warm to ambient temperature and stood overnight at this temperature. The solvent was removed under reduced pressure and the solid residue obtained was washed with water and filtered. The residue was triturated with hot ethyl acetate, collected by filtration and identified by LCMS as ∝-[4-(4-amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl]benzyl alcohol, m.p. 279-281° C.

Workup

  1. additionAfter the addition the mixture
  2. temperaturemaintained at this temperature for 40 minutes
  3. customThe reaction was quenched by the dropwise addition of saturated ammonial chloride solution (4 ml) at 0° C
  4. temperatureto warm to ambient temperature
  5. customThe solvent was removed under reduced pressure
  6. customthe solid residue obtained
  7. washwas washed with water
  8. filtrationfiltered
  9. customThe residue was triturated with hot ethyl acetate
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ad7411334f0e4afca76d2e728954badf
Source dataset
uspto-grants-2011_01
Patent number
US07863444B2

Reaction notes

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