Carbon Dioxide → HCID 86685440, compound

HRID 876646Notes

Reaction equation

HRID 876646 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7](=O)=O.C(O[C:13]([C:15]1[C:16]([NH:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=N[C:18]([S:21][CH3:22])=[N:19][CH:20]=1)=[O:14])C>C1COCC1>[CH:24]1([NH:23][C:16]2[C:15]([CH2:13][OH:14])=[CH:20][N:19]=[C:18]([S:21][CH3:22])[CH:7]=2)[CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 9151473Ethyl 4-(cyclopentylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 86685440HCID 86685440, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (10 g, 35.5 mmol) was suspended in THF under a nitrogen atmosphere and cooled with dry ice. 4-Cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (7), (2.02 g, 53.3 mmol) was dissolved in THF and added dropwise to the cooled LAH solution, keeping the reaction temperature below −20° C. for the duration of the addition. The reaction was subsequently brought to room temperature and stirred for 5 h. After stirring, the reaction was quenched by the addition of water (5 ml), 15% NaOH (10 ml) and then water (15 ml) again. A white solid that precipitated was filtered away and the filtrate evaporated in vacuo to provide product (8) as a yellow solid (7.2 g). Product (8) was used without further purification or characterization.

Workup

  1. customthe reaction temperature below −20° C.
  2. additionfor the duration of the addition
  3. customwas subsequently brought to room temperature
  4. stirringAfter stirring
  5. customthe reaction was quenched by the addition of water (5 ml), 15% NaOH (10 ml)
  6. customA white solid that precipitated
  7. filtrationwas filtered away
  8. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-4baf98c2d6dc44ddb6b70a72f43183c8
Source dataset
uspto-grants-2015_03
Patent number
US08987267B2

Reaction notes

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