Thiourea → 4-[7-(Toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-thiazol-2-ylamine

HRID 400562Notes

Reaction equation

HRID 400562 reaction equation
Br[CH2:2][C:3]([C:5]1[C:6]2[CH:13]=[CH:12][N:11]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C:7]=2[N:8]=[CH:9][N:10]=1)=O.[NH2:24][C:25]([NH2:27])=[S:26]>CC(C)=O>[C:20]1([CH3:23])[CH:21]=[CH:22][C:17]([S:14]([N:11]2[C:7]3[N:8]=[CH:9][N:10]=[C:5]([C:3]4[N:24]=[C:25]([NH2:27])[S:26][CH:2]=4)[C:6]=3[CH:13]=[CH:12]2)(=[O:16])=[O:15])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 586917252-Bromo-1-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-ethanone

Product 1

HCID 576473414-[7-(Toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-thiazol-2-ylamineYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into 75 mL of acetone was successively added [4.2 g, 10.65 mmol] of 2-Bromo-1-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-ethanone followed by [0.81 g, 10.65 mmol] of thiourea. The reaction was then stirred for 4.0 hours at ambient temperature. The pale yellow precipitate was collected via suction filtration and washed with more acetone. The crude cake was suspended into 20 mL of triethylamine and stirred for one hour. The material was then diluted with water and suction filtered to isolate the solid. The damp cake was triturated with acetonitrile, the solid isolated again via suction filtration and airdried. The beige solid, 2.6 g, represents a 72% yield of the free base.

Workup

  1. filtrationThe pale yellow precipitate was collected via suction filtration
  2. washwashed with more acetone
  3. stirringstirred for one hour
  4. additionThe material was then diluted with water and suction
  5. filtrationfiltered
  6. customto isolate the solid
  7. customThe damp cake was triturated with acetonitrile
  8. customthe solid isolated again via suction filtration

Sources & evidence

ORD record
ord-f26f772ce7e94dec86d855925a234789
Source dataset
uspto-grants-2014_06
Patent number
US08741912B2

Reaction notes

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