Sodium ethoxide → HCID 15547258, compound

HRID 854252Notes

Reaction equation

HRID 854252 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[N:13]=[C:14]([CH3:38])[N:15]=[C:16]([NH:17][CH2:18][C@H:19]([NH:27][C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])[C:20]([O:22]C(C)(C)C)=[O:21])[C:11]=2[CH:10]=[CH:9]1)C.C([O-])C.[Na+].[NH2:44][C:45]1[NH:46][CH2:47][CH2:48][CH2:49][N:50]=1>C1COCC1>[CH2:31]([O:30][C:28]([NH:27][C@@H:19]([CH2:18][NH:17][C:16]1[C:11]2[CH:10]=[CH:9][N:8]([CH2:7][CH2:6][CH2:5][C:4](=[O:3])[NH:44][C:45]3[NH:50][CH2:49][CH2:48][CH2:47][N:46]=3)[C:12]=2[N:13]=[C:14]([CH3:38])[N:15]=1)[C:20]([OH:22])=[O:21])=[O:29])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineHCID 15546709HCID 15546709, compound

Product 1

HCID 15547258HCID 15547258, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 300 mg (0.5 mmol) of 4-[4-((2S)-2-benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylamino)-2-methyl-pyrrolo[2,3-d]pyrimidin-7-yl]-butyric acid ethyl ester (example 2b) in 5 ml of absol. THF were added 124 mg (1.82 mmol) of sodium ethanolate and 155 mg (1.56 mmol) of 1,4,5,6-tetrahydro-2-aminopyrimidine and the solution was stirred at room temperature for 6 hours. The mixture was brought to pH 7.0 and the solvent was removed in vacuo. The residue was chromatographed on silica gel eluting with DCM/MeOH/AcOH/H2O (90:10:1:1). Yield: 28 mg.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was chromatographed on silica gel eluting with DCM/MeOH/AcOH/H2O (90:10:1:1)

Sources & evidence

ORD record
ord-a9a88295bdb240b290a7c5628fe267ec
Source dataset
uspto-grants-2007_08
Patent number
US07259159B2

Reaction notes

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