Trityl chloride → Amino(1-triphenylmethyl-1,4,5,6-tetrahydropyrimidin-5-yl)acetamide

HRID 1681903Notes

Reaction equation

HRID 1681903 reaction equation
Cl.Cl.[NH2:3][CH:4]([CH:8]1[CH2:13][NH:12][CH:11]=[N:10][CH2:9]1)[C:5]([NH2:7])=[O:6].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.[C:36](Cl)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C=O)C>[NH2:3][CH:4]([CH:8]1[CH2:13][N:12]([C:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:11]=[N:10][CH2:9]1)[C:5]([NH2:7])=[O:6]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 20080419Amino(1,4,5,6-tetrahydropyrimidine-5-yl)acetamide dihydrochlorideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 20080439Amino(1-triphenylmethyl-1,4,5,6-tetrahydropyrimidin-5-yl)acetamideYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Amino(1,4,5,6-tetrahydropyrimidine-5-yl)acetamide dihydrochloride (1.33 g, 5.8 mmol), diazabicycloundecene (DBU, 2.6 ml, 17.4 mmol), and tritylchloride (1.61 g, 5.8 mmol) are dissolved in anhydrous DMF (20 ml) with stirring under nitrogen at room temperature. After 18 hours stirring the suspension is evaporated in vacuo, and the residue chromatographed (silica, chloroform/methanol, 9:1) to yield 1.64 g (71%) white crystalline solid, identified by 300 MHz nmr and ms m/z=398.

Workup

  1. stirringAfter 18 hours stirring the suspension
  2. customis evaporated in vacuo
  3. customthe residue chromatographed (silica, chloroform/methanol, 9:1)

Sources & evidence

ORD record
ord-1521d6b8182b4267b523d3cb220fc94c
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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