Cesium carbonate → HCID 21882944, compound

HRID 722108Notes

Reaction equation

HRID 722108 reaction equation
Br[CH2:2][C:3]1[S:4][C:5]2[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:13][C:14]1[N:22]=[C:21]2[C:17]([NH:18][CH:19]=[N:20]2)=[C:16]([Cl:23])[N:15]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:23][C:16]1[N:15]=[C:14]([NH2:13])[N:22]=[C:21]2[C:17]=1[N:18]=[CH:19][N:20]2[CH2:2][C:3]1[S:4][C:5]2[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 53603492-Amino-6-chloropurineHCID 218828992-(Bromomethyl)-7-chloro-1,3-benzothiazole

Product 1

HCID 21882944HCID 21882944, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-bromomethyl-7-chloro-benzothiazole (60 mg, 0.2286 mmol), 2-amino-6-chloropurine (32 mg, 0.19 mmol), Cs2CO3 (67.86 mg, 0.208 mmol), and DMF (2 ml) was heated to 40° C. for 1 h. The reaction was cooled to r.t. and the solvent was removed on a rotary evaporator. The resulting solid was purified by preparative TLC to give the title compound (50 mg, 0.14 mmol). HPLC Rt: 5.81 min. 1H-NMR (CDCl3): δ 8.0 (s, 1H), 7.95 (d, 1H), 7.48 (t, 1H), 7.43 (d, 1H), 5.69 (s, 2H), 5.17 (s, 2H).

Workup

  1. temperatureThe reaction was cooled to r.t.
  2. customthe solvent was removed on a rotary evaporator
  3. customThe resulting solid was purified by preparative TLC

Sources & evidence

ORD record
ord-cf1ff918c4b540678105c49cf51551b6
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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