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

HRID 2262311Notes

Reaction equation

HRID 2262311 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-f629f4baf7484421beecd60f3c60d190
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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