HCID 57929486, compound → HCID 44465926, compound

HRID 2386688Notes

Reaction equation

HRID 2386688 reaction equation
[CH3:1][O:2][C:3](=[O:35])[NH:4][CH:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[C:21]([NH2:22])=[CH:20][C:19](=[O:23])[N:18]([CH2:24][CH2:25][CH2:26][O:27][Si](C(C)(C)C)(C)C)[C:16]=3[N:17]=2)[CH2:7][CH2:6]1>C(O)(=O)C.C1COCC1.O>[CH3:1][O:2][C:3](=[O:35])[NH:4][CH:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[C:21]([NH2:22])=[CH:20][C:19](=[O:23])[N:18]([CH2:24][CH2:25][CH2:26][OH:27])[C:16]=3[N:17]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 1

HCID 57929486HCID 57929486, compound

Product 1

HCID 44465926HCID 44465926, compoundYield 10.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(4-{5-Amino-8-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino}-cyclohexyl)-carbamic acid methyl ester (prepared as described in Example 2) (0.280 mmol) was dissolved in a mixture of glacial acetic acid, THF and water (3/1/1, 25 mL) and the resulting mixture was stirred at RT overnight. The reaction mixture was concentrated under reduced pressure and the crude residue was purified by preparative TLC (MeOH/DCM, 15/85) to give 11 mg of {4-[5-amino-8-(3-hydroxy-propyl)-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-cyclohexyl}-carbamic acid methyl ester as a yellow powder. MS=391 [M+H]+; MP=190.0-191.0° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude residue was purified by preparative TLC (MeOH/DCM, 15/85)

Sources & evidence

ORD record
ord-5fcdec15f8814f298682c761b69c8458
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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