Chloroacetone → HCID 59468431, compound

HRID 1012183Notes

Reaction equation

HRID 1012183 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[S:9][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)[N:14]=2)=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:31][C:32](=[O:34])[CH3:33]>CN(C=O)C>[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:31][C:32](=[O:34])[CH3:33])[C:8]1[S:9][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)[N:14]=2)=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6571Chloroacetone2×HCID 24758Sodium hydride2×HCID 59468607HCID 59468607, compound

Product 1

HCID 59468431HCID 59468431, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

[5-(2-m-Tolylamino-pyrimdin-4-yl)-thiophen-2-yl]-carbamic acid tert-butyl ester (30 mg, 0.078 mmol) was dissolved in DMF (0.8 mL) and 60% NaH (4.7 mg, 0.117 mmol) was added. After 8 min., KI (12.9 mg, 0.078 mmol) and chloroacetone (9.4 uL, 0.117 mmol) were added and the reaction was heated to 60° C. for 15 h. The reaction was ˜60% converted and an additional aliquot of 60% NaH (3.1 mg, 0.078 mmol) and chloroacetone (6.2 uL, 0.078 mmol) were added and reaction heated at 60° C. for another 18 h. The reaction was concentrated in vacuo and taken to the next step crude.

Workup

  1. customreaction
  2. temperatureheated at 60° C. for another 18 h
  3. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-8887069472e044d6a4898a69a1370f87
Source dataset
uspto-grants-2011_07
Patent number
US07977481B2

Reaction notes

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