Triphosgene → tert-Butyl 3-(6-(dibenzylamino)-8-oxo-7H-purin-9(8H)-yl)phenylcarbamate

HRID 1887040Notes

Reaction equation

HRID 1887040 reaction equation
[NH2:1][C:2]1[C:3]([NH:23][C:24]2[CH:25]=[C:26]([NH:30][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:39](Cl)([O:41]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:39](=[O:41])[N:23]2[C:24]1[CH:25]=[C:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:36])[CH3:35])[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 86691211Tert-butyl 3-(5-amino-6-(dibenzylamino)pyrimidin-4-ylamino)phenylcarbamate

Product 1

HCID 86691210tert-Butyl 3-(6-(dibenzylamino)-8-oxo-7H-purin-9(8H)-yl)phenylcarbamateYield 143.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl 3-(5-amino-6-(dibenzylamino)pyrimidin-4-ylamino)phenylcarbamate (3) (4.0 g, 8.1 mmol) and TEA (2 mL, 14.5 mmol) in 80 mL dry DCM was cooled to 0° C. under N2, triphosgene (1.2 g, 4.0 mmol) in 10 mL dry DCM was added dropwise during 2 hrs. After additional 1 hr stirring, the reaction was quenched with water (100 mL). The organic layer was separated, washed with water (100 mL×2) and brine (100 mL×1), dried over Na2SO4, then concentrated to dryness in vacuo. tert-Butyl 3-(6-(dibenzylamino)-8-oxo-7H-purin-9(8H)-yl)phenylcarbamate (4) (3.0 g, 71%) was obtained as a brown solid. LC-MS (ESI): m/z (M+1) 523.

Workup

  1. customthe reaction was quenched with water (100 mL)
  2. customThe organic layer was separated
  3. washwashed with water (100 mL×2) and brine (100 mL×1)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-c906fd43377b4c008162d1e13efa1096
Source dataset
uspto-grants-2013_08
Patent number
US08501724B1

Reaction notes

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