1,4,5,6-Tetrahydropyrimidin-2-amine → (2s)-2-(1-Adamantylmethoxycarbonylamino)-3-((5-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-thiophene-2-carbonyl)-amino)-propionic acid tert-butyl ester

HRID 413220Notes

Reaction equation

HRID 413220 reaction equation
[C:1]([O:5][C:6](=[O:38])[C@@H:7]([NH:23][C:24]([O:26][CH2:27][C:28]12[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH2:29]1)[CH2:35]2)=[O:25])[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19]([O:21]C)=O)=[CH:15][CH:16]=1)=[O:11])([CH3:4])([CH3:3])[CH3:2].[NH2:39][C:40]1[NH:41][CH2:42][CH2:43][CH2:44][N:45]=1>CN(C)C=O>[C:1]([O:5][C:6](=[O:38])[C@@H:7]([NH:23][C:24]([O:26][CH2:27][C:28]12[CH2:29][CH:30]3[CH2:36][CH:34]([CH2:33][CH:32]([CH2:31]3)[CH2:37]1)[CH2:35]2)=[O:25])[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19](=[O:21])[NH:39][C:40]2[NH:45][CH2:44][CH2:43][CH2:42][N:41]=2)=[CH:15][CH:16]=1)=[O:11])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineHCID 69637234(2s)-2-(1-Adamantylmethoxycarbonylamino)-3-((5-(2-methoxycarbonyl-ethyl)-thiophene-2-carbonyl)-amino)-propionic acid tert-butyl ester

Product 1

HCID 69637241(2s)-2-(1-Adamantylmethoxycarbonylamino)-3-((5-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-thiophene-2-carbonyl)-amino)-propionic acid tert-butyl esterYield 71.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.37 g (2.5 mmol) of the product obtained in step b) were dissolved in 12 ml of anhydrous dimethylformamide, and after addition of 1.24 g of 2-amino-1,4,5,6-tetrahydropyrimidine the mixture was stirred at room temperature for 5 hours. The solvent was removed in vacuo and the residue was chromatographed (silica gel; ethyl acetate/methanol (1/1; v/v)) to give 1.1 g of the title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed (silica gel; ethyl acetate/methanol (1/1; v/v))

Sources & evidence

ORD record
ord-70a9e86534f24f21973eabf693f46a8f
Source dataset
uspto-grants-2003_05
Patent number
US06566366B1

Reaction notes

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