Thiourea → 4-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)thiazol-2-amine

HRID 2098879Notes

Reaction equation

HRID 2098879 reaction equation
Br[CH2:2][C:3]([C:5]1[S:13][C:12]2[C:11]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:10][C:9]([Cl:20])=[N:8][C:7]=2[CH:6]=1)=O.[NH2:21][C:22]([NH2:24])=[S:23]>CCO>[Cl:20][C:9]1[N:10]=[C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:12]2[S:13][C:5]([C:3]3[N:21]=[C:22]([NH2:24])[S:23][CH:2]=3)=[CH:6][C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 595929052-Bromo-1-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)ethanone

Product 1

HCID 595929714-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-bromo-1-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)ethanone (1.0 eq) dissolved in EtOH was added thiourea. Reaction mixture was heated at 70° C. until completed, then extracted in dichloromethane with saturated bicarbonate solution one time. The organic layer is dried, filtered and concentrated to yield the crude intermediate. This intermediate is purified by flash chromatography to yield 4-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)thiazol-2-amine. MS (Q1) 413 (M+)

Workup

  1. customReaction mixture
  2. extractionextracted in dichloromethane with saturated bicarbonate solution one time
  3. customThe organic layer is dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield the crude intermediate
  7. customThis intermediate is purified by flash chromatography

Sources & evidence

ORD record
ord-dc9e3e1ba69c47f48caf7a02b7dfc8ca
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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