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

HRID 1653710Notes

Reaction equation

HRID 1653710 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 (1.49 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-d701dcc8b3bd447c89a728af87a1f7a1
Source dataset
uspto-grants-1995_04
Patent number
US05403845

Reaction notes

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