HCID 117778962, compound → HCID 117779063, compound

HRID 1527127Notes

Reaction equation

HRID 1527127 reaction equation
C(OC(N1CCC(C(N2C3N=CN=CC=3C(C([O-])=O)=C2C)C)CC1)=O)(C)(C)C.[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][CH:39]([CH:42]([N:44]2[C:48]3[N:49]=[C:50](Cl)[N:51]=[CH:52][C:47]=3[C:46]([C:54]([O:56][CH2:57][CH3:58])=[O:55])=[C:45]2[CH3:59])[CH3:43])[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].[H][H]>CO.[Pd]>[C:29]([O:33][C:34]([N:36]1[CH2:37][CH2:38][CH:39]([CH:42]([N:44]2[C:48]3[N:49]=[CH:50][N:51]=[CH:52][C:47]=3[C:46]([C:54]([O:56][CH2:57][CH3:58])=[O:55])=[C:45]2[CH3:59])[CH3:43])[CH2:40][CH2:41]1)=[O:35])([CH3:31])([CH3:32])[CH3:30]

Participants

6

Reactant 3

HCID 117778962HCID 117778962, compoundHCID 131733199HCID 131733199, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 117779063HCID 117779063, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tethyl 7-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)ethyl)-6-methyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, Intermediate 9. A mixture of compound ethyl 7-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)ethyl)-2-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (75 mg, 0.16 mmol) and Pd/C(10 mg) in methanol (10 mL) was stirred under 50 psi of hydrogen at room temperature overnight. The reaction mixture was filtered and the filtrate was concentrated to give product ethyl 7-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)ethyl)-6-methyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (50 mg, yield: 72%). LRMS (M+H+) m/z: calcd 450.2. found 451.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e4cc0b93d60941f6841a2e63e36c6ab5
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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