Dimethylformamide → HCID 58015786, compound

HRID 2189339Notes

Reaction equation

HRID 2189339 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([NH2:14])=[CH:4][N:3]=1.CN([CH:18]=[O:19])C.C(N1C=CN=C1)(N1C=CN=C1)=O>CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]2[C:5]([NH:14][C:18](=[O:19])[N:8]2[CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 58016005HCID 58016005, compound

Product 1

HCID 58015786HCID 58015786, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a microwave vial is added the crude (2-chloro-5-amino-pyrimidin-4-yl)-(1-ethyl-propyl)-amine (0.5 g, 2.3 mmol) and anhydrous DMF (15 mL) followed by 1,1′-carbonyldiimidazole (1.1 g, 7.0 mmol). Sealed vial and microwave are heated at 100° C. for 10 min. The reaction mixture is diluted with EtOAc, washed with water, dried over Na2SO4, and concentrated in vacuo. Purification with column chromatography (SiO2, EtOAC/Hexane 1:1) gives 0.3 g of 2-chloro-9-(1-ethyl-propyl)-7,9-dihydro-purin-8-one. LCMS: 241.1 (M+H)+

Workup

  1. customSealed vial
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification with column chromatography (SiO2, EtOAC/Hexane 1:1)

Sources & evidence

ORD record
ord-6e10df0ae0d742a6923c83824c8dd42d
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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