Trityl chloride → 1-Triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

HRID 1681877Notes

Reaction equation

HRID 1681877 reaction equation
Cl.[CH3:2][O:3][C:4]([CH:6]1[CH2:11][NH:10][CH:9]=[N:8][CH2:7]1)=[O:5].N12CCCN=C1CCCCC2.[C:23](Cl)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[C:24]1([C:23]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:8]2[CH2:7][CH:6]([C:4]([O:3][CH3:2])=[O:5])[CH2:11][N:10]=[CH:9]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199620591,4,5,6-Tetrahydro-5-methoxycarbonylpyrimidine Hydrochloride

Product 1

HCID 100455711-Triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,4,5,6-Tetrahydro-5-methoxycarbonylpyrimidine hydrochloride (I.49 g, 8.3 mmol), 1,8 diazabicyclo [5.4.0] undec-7ene, (hereinafter diazabicycloundecene and/or DBU), (2.5 mL, 16.6 mmol), and tritylchloride (2.32 g, 8.3 mmol) were suspended in anhydrous DMF (20 ml) with stirring under nitrogen at room temperature. After 18 hours stirring the suspension was evaporated in vacuo and the residue chromatographed (silica, chloroform/methanol, 9:1) to yield 2.28 g (rf=0.15, 71%) white crystalline solid identified by 300 MHz nmr and ms m/z=384.

Workup

  1. stirringAfter 18 hours stirring the suspension
  2. customwas evaporated in vacuo
  3. customthe residue chromatographed (silica, chloroform/methanol, 9:1)
  4. customto yield 2.28 g (rf=0.15, 71%) white crystalline solid

Sources & evidence

ORD record
ord-3677f87c329c43c5b9803f40d39767d9
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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