Cesium carbonate → HCID 67242092, compound

HRID 1970400Notes

Reaction equation

HRID 1970400 reaction equation
[C:1]([NH:5][C:6]1[S:7][CH2:8][C:9]2([N:30]=1)[C:22]1[CH:21]=[C:20]([OH:23])[CH:19]=[CH:18][C:17]=1[O:16][C:15]1[C:10]2=[CH:11][C:12]([C:24]2[CH:25]=[N:26][CH:27]=[N:28][CH:29]=2)=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40]>CN(C=O)C.CCOC(C)=O>[C:1]([NH:5][C:6]1[S:7][CH2:8][C:9]2([N:30]=1)[C:22]1[CH:21]=[C:20]([O:23][CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH:19]=[CH:18][C:17]=1[O:16][C:15]1[C:10]2=[CH:11][C:12]([C:24]2[CH:25]=[N:26][CH:27]=[N:28][CH:29]=2)=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 84953Propane, 1-iodo-2,2-dimethyl-HCID 67247986HCID 67247986, compound

Product 1

HCID 67242092HCID 67242092, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(tert-butylamino)-7′-(pyrimidin-5-yl)-5H-spiro[thiazole-4,9′-xanthen]-2′-ol (0.075 g, 0.179 mmol) in DMF (2 mL) was added cesium carbonate (0.175 g, 0.538 mmol) followed by 1-iodo-2,2-dimethylpropane (0.048 mL, 0.358 mmol). The mixture was heated to 100° C. After 6 hrs the mixture was cooled to RT, diluted with EtOAc, and washed with water and brine. The organic fraction was concentrated in vacuo and purified by silica gel chromatography using 40-60% Hexanes:EtOAc to afford N-tert-butyl-2′-(neopentyloxy)-7′-(pyrimidin-5-yl)-5H-spiro[thiazole-4,9′-xanthen]-2-amine as an off-white foam. MS: MH+=489.2.

Workup

  1. temperatureAfter 6 hrs the mixture was cooled to RT
  2. washwashed with water and brine
  3. concentrationThe organic fraction was concentrated in vacuo
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-82a74c73cfc34c439c7cffa2486bd1ce
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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