Hydrochloric Acid → N-(2-(2-Aminothiazol-5-yl)ethyl)thieno[3,2-d]pyrimidin-4-amine

HRID 1818924Notes

Reaction equation

HRID 1818924 reaction equation
C(OC(=O)[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)(C)(C)C.Cl>O1CCOCC1>[NH2:7][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

Participants

4

Reactant 2

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

Product 1

HCID 44230296N-(2-(2-Aminothiazol-5-yl)ethyl)thieno[3,2-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of compound 14.2 (14.5 mmol) in 1,4-dioxane (30 mL) was added anhydrous HCl (20 mL of a 4 N solution in 1,4-dioxane) after stirring at room temperature for 2 hours the reaction was concentrated to dryness, diluted with water and the solution adjusted to pH 8 with saturated sodium bicarbonate. The slurry was extracted several times with EtOAc and the organic layers were combined, dried and concentrated to provide [2-(2-amino-thiazol-5-yl)-ethyl]-thieno[3,2-d]pyrimidin-4-yl-amine (compound 14.3) in 88% yield.

Workup

  1. concentrationwas concentrated to dryness
  2. additiondiluted with water
  3. extractionThe slurry was extracted several times with EtOAc
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a67880b5f57646fca3e479f89a4124b7
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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