HCID 66760787, compound → HCID 86662393, compound

HRID 1188708Notes

Reaction equation

HRID 1188708 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([NH:12][C:13]1[C:18]([CH2:19][OH:20])=[CH:17][N:16]=[C:15]([S:21][CH3:22])[N:14]=1)[CH2:9][CH2:8]2>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([NH:12][C:13]1[C:18]([CH:19]=[O:20])=[CH:17][N:16]=[C:15]([S:21][CH3:22])[N:14]=1)[CH2:9][CH2:8]2

Participants

4

Reactant 1

HCID 66760787HCID 66760787, compound

Product 1

HCID 86662393HCID 86662393, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-(7-methoxy-2,3-dihydro-1H-inden-1-ylamino)-2-(methylthio)pyrimidin-5-yl)methanol (2.36 g, 7.43 mmol) in dichloromethane (80 mL) was added manganese dioxide (90%, 3.87 g, 40 mmol) in small portions. The resulting suspension was stirred for 18 h. Additional manganese dioxide (90%, 3.87 g, 40 mmol) was added and the mixture was stirred for an additional 18 h. The mixture was filtered through Celite and washed with dichloromethane (5×10 mL). The combined filtrates were evaporated in vacuo to give 4-(7-methoxy-2,3-dihydro-1H-inden-1-ylamino)-2-(methylthio)pyrimidine-5-carbaldehyde as a light brown solid (1.89 g, 5.99 mmol, 80%). ESMS m/z 316 (M+H)+.

Workup

  1. stirringthe mixture was stirred for an additional 18 h
  2. filtrationThe mixture was filtered through Celite
  3. washwashed with dichloromethane (5×10 mL)
  4. customThe combined filtrates were evaporated in vacuo

Sources & evidence

ORD record
ord-a23c0fb1023d4c69b9f5be09ce4c6f04
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

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