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

HRID 413217Notes

Reaction equation

HRID 413217 reaction equation
C[O:2][C:3]([CH:5]1[CH2:7][CH:6]1[C:8]1[S:9][C:10]([C:13](=[O:39])[NH:14][CH2:15][C@H:16]([NH:24][C:25]([O:27][CH2:28][C:29]23[CH2:38][CH:33]4[CH2:34][CH:35]([CH2:37][CH:31]([CH2:32]4)[CH2:30]2)[CH2:36]3)=[O:26])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:11][CH:12]=1)=O.[NH2:40][C:41]1[NH:42][CH2:43][CH2:44][CH2:45][N:46]=1>CN(C)C=O>[C:20]([O:19][C:17](=[O:18])[C@@H:16]([NH:24][C:25]([O:27][CH2:28][C:29]12[CH2:38][CH:33]3[CH2:32][CH:31]([CH2:37][CH:35]([CH2:34]3)[CH2:36]1)[CH2:30]2)=[O:26])[CH2:15][NH:14][C:13]([C:10]1[S:9][C:8]([CH:6]2[CH2:7][CH:5]2[C:3](=[O:2])[NH:40][C:41]2[NH:46][CH2:45][CH2:44][CH2:43][N:42]=2)=[CH:12][CH:11]=1)=[O:39])([CH3:21])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineHCID 572486992-(5-(((2s)-2-(1-Adamantylmethoxycarbonylamino)-2-tert-butoxycarbonyl-ethyl)carbamoyl)-2-thienyl)-cyclopropancarboxylic acid methyl ester

Product 1

HCID 69637307(2s)-2-(1-Adamantylmethoxycarbonylamino)-3-((5-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-cyclopropyl)-thiophene-2-carbonyl)-amino)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product obtained in step b) was dissolved in 4 ml of anhydrous dimethylformamide and stirred under an argon atmosphere with 99 mg of 2-amino-1,4,5,6-tetrahydropyrimidine for 7 hours at room temperature. The solvent was removed in vacuo and the residue was chromatographed (silica gel; ethyl acetate/methanol (1/1, v/v)). The fractions containing the title compound were pooled and evaporated under reduced pressure to give 53 mg of a colourless resin.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed (silica gel
  3. additionThe fractions containing the title compound
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2ea1e4f7f98d4e6fb141bc95e900c231
Source dataset
uspto-grants-2003_05
Patent number
US06566366B1

Reaction notes

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