Dimethylamine → HCID 57476593, compound

HRID 250107Notes

Reaction equation

HRID 250107 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:10]=[C:9]([NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])[S:8][C:6]=2[N:7]=1.[CH3:17][NH:18][CH3:19].CO>>[CH3:17][N:18]([CH3:19])[C:2]1[N:3]=[CH:4][C:5]2[N:10]=[C:9]([NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])[S:8][C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 887MethanolHCID 57476592HCID 57476592, compound

Product 1

HCID 57476593HCID 57476593, compoundYield 99%

Conditions

Temperature
75 °C

Procedure

Ethyl 5-chlorothiazolo[5,4-d]pyrimidin-2-ylcarbamate (300 mg, 1.16 mmol) was suspended in a 2.0 M solution of dimethylamine in methanol (5.0 mL, 10.00 mmol) in a pressure vessel, which was sealed and heated overnight on a 75° C. oil bath. The mixture was cooled to ambient temperature, the solvent was evaporated and the residue was partitioned between aqueous bicarbonate and chloroform and extracted 3 times. The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford ethyl 5-(dimethylamino)thiazolo[5,4-d]pyrimidin-2-ylcarbamate (236 mg, 99% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.97 (s, 1H) 8.67 (s, 1H) 4.26 (q, J=7.03 Hz, 2H) 3.17 (s, 6H) 1.16-1.40 (m, 3H). MS (LC/MS) R.T.=1.88; [M+H]+=268.09.

Workup

  1. customwhich was sealed
  2. temperatureThe mixture was cooled to ambient temperature
  3. customthe solvent was evaporated
  4. customthe residue was partitioned between aqueous bicarbonate and chloroform
  5. extractionextracted 3 times
  6. washThe combined organics were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2c8a67dec4d4f56863662d07131445f
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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