Triphosgene → tert-butyl 3-(6-(dibenzylamino)-8-oxo-7H-purin-9(8H)-yl)phenyl(methyl)carbamate

HRID 1887052Notes

Reaction equation

HRID 1887052 reaction equation
[NH2:1][C:2]1[C:3]([NH:23][C:24]2[CH:25]=[C:26]([N:30]([CH3:38])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH:27]=[CH:28][CH:29]=2)=[N:4][CH:5]=[N:6][C:7]=1[N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl[C:40](Cl)([O:42]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH2:16]([N:8]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:7]1[N:6]=[CH:5][N:4]=[C:3]2[C:2]=1[NH:1][C:40](=[O:42])[N:23]2[C:24]1[CH:25]=[C:26]([N:30]([CH3:38])[C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH:27]=[CH:28][CH:29]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 86691217Tert-butyl 3-(5-amino-6-(dibenzylamino)pyrimidin-4-ylamino)phenyl(methyl)carbamate

Product 1

HCID 86691216tert-butyl 3-(6-(dibenzylamino)-8-oxo-7H-purin-9(8H)-yl)phenyl(methyl)carbamateYield 230.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of tert-butyl 3-(5-amino-6-(dibenzylamino)pyrimidin-4-ylamino)phenyl(methyl)carbamate (22) (3.1 g, 6.08 mmol) and TEA (1.75 mL, 12.16 mmol) in dry DCM (40 mL) at 0° C. and under N2 atmosphere was added a solution of triphosgene (722 mg, 2.43 mmol) in dry DCM (20 mL) dropwise during 1 h. After the stirring was continued for 1 h, the reaction was quenched with water (10 mL). The organic layer was separated, washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 0 to 20% ethyl acetate in petroleum ether) to give tert-butyl 3-(6-(dibenzylamino)-8-oxo-7H-purin-9(8H)-yl)phenyl(methyl)carbamate (23) (3 g, 92%) as a light brown solid. LC-MS (ESI): m/z (M+1) 537.

Workup

  1. customthe reaction was quenched with water (10 mL)
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, 0 to 20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-5b3f7cb488834a14ada8590961cad22d
Source dataset
uspto-grants-2013_08
Patent number
US08501724B1

Reaction notes

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