Hydrochloric Acid → {5-[2-(Thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid phenyl ester

HRID 1818925Notes

Reaction equation

HRID 1818925 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[S:9][C:10]([CH2:13][CH2:14][NH:15][C:16]2[C:17]3[S:24][CH:23]=[CH:22][C:18]=3[N:19]=[CH:20][N:21]=2)=[CH:11][N:12]=1)([CH3:4])([CH3:3])C.Cl.C(N(CC)CC)C.ClC(O[C:38]1[CH:43]=CC=C[CH:39]=1)=O>O1CCOCC1.C1COCC1>[C:1]1([O:5][C:6](=[O:25])[NH:7][C:8]2[S:9][C:10]([CH2:13][CH2:14][NH:15][C:16]3[C:17]4[S:24][CH:23]=[CH:22][C:18]=4[N:19]=[CH:20][N:21]=3)=[CH:11][N:12]=2)[CH:3]=[CH:43][CH:38]=[CH:39][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 86603168{5-[2-(Thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester

Product 1

HCID 86603169{5-[2-(Thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid phenyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of compound 14.2 (23.7 mmol) in 1,4-dioxane (100 mL) was added HCl (70 mL of a 4.0 M in 1,4-dioxane) at 0° C. The reaction was allowed to warm to room temperature, stirred for 2 hours and concentrated to dryness to give a tan solid. The crude solid was suspended in THF (200 mL) and cooled to 0° C. Triethylamine (33 mL) was added followed by phenyl chloroformate (26.1 mmol). The reaction mixture was allowed to slowly warm to room temperature and stirred for 2 hours. Volatiles were removed under reduced pressure at room temperature, water was added and the solid collected by vacuum filtration. The solid was washed with ethyl ether and dried under vacuum to give {5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid phenyl ester (compound 16.1) in 80% yield as a tan solid.

Workup

  1. concentrationconcentrated to dryness
  2. customto give a tan solid
  3. temperaturecooled to 0° C
  4. temperatureto slowly warm to room temperature
  5. stirringstirred for 2 hours
  6. customVolatiles were removed under reduced pressure at room temperature
  7. additionwater was added
  8. filtrationthe solid collected by vacuum filtration
  9. washThe solid was washed with ethyl ether
  10. customdried under vacuum

Sources & evidence

ORD record
ord-a798282908d04f38bbfbded3907c4112
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

Loading…