Pyrimidin-5-amine → (S)-Benzyl 1-(3-bromo-2-(pyrimidin-5-ylcarbamoyl)-1H-pyrrol-1-ylamino)-1-oxopropan-2-ylcarbamate

HRID 525032Notes

Reaction equation

HRID 525032 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH3:26])[C:13]([NH:15][N:16]1[CH:20]=[CH:19][C:18]([Br:21])=[C:17]1[C:22]([O:24]C)=O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:27]1[CH:32]=[C:31]([NH2:33])[CH:30]=[N:29][CH:28]=1>>[Br:21][C:18]1[CH:19]=[CH:20][N:16]([NH:15][C:13](=[O:14])[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:26])[C:17]=1[C:22](=[O:24])[NH:33][C:31]1[CH:32]=[N:27][CH:28]=[N:29][CH:30]=1

Participants

3

Reactant 2

HCID 344373Pyrimidin-5-amineHCID 86722049(S)-Methyl 1-(2-(benzyloxycarbonylamino)propanamido)-3-Bromo-1H-Pyrrole-2-carboxylate

Product 1

HCID 86722051(S)-Benzyl 1-(3-bromo-2-(pyrimidin-5-ylcarbamoyl)-1H-pyrrol-1-ylamino)-1-oxopropan-2-ylcarbamateYield 62.3%

Procedure

The title compound was prepared from (S)-methyl 1-(2-(benzyloxycarbonylamino)propanamido)-3-bromo-1H-pyrrole-2-carboxylate (0.81 g, 1.91 mmol) and pyrimidin-5-amine (1.45 g, 15.3 mmol) following the experimental procedure described in Preparation 44a. 0.58 g (62% yield) of the desired compound were obtained.

Sources & evidence

ORD record
ord-637bc35940f1483fa25b529fd4e47e68
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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