Phosphorus oxychloride → 2-chloro-9-(2,2-dimethyl-propyl)-8-methyl-9H-purine

HRID 271626Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[C:5]([NH2:14])=[CH:4][N:3]=1.O=P(Cl)(Cl)Cl.[CH3:20][C:21](N(C)C)=O>>[Cl:1][C:2]1[N:7]=[C:6]2[C:5]([N:14]=[C:20]([CH3:21])[N:8]2[CH2:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[CH:4][N:3]=1

Participants

Reactant 3

HCID 24813Phosphorus oxychloride

HCID 31374Dimethylacetamide

HCID 179682102-Chloro-N4-(2,2-dimethylpropyl)-4,5-pyrimidinediamine

Product 1

HCID 179682662-chloro-9-(2,2-dimethyl-propyl)-8-methyl-9H-purine

Conditions

Temperature: 100 °C

Procedure

To a solution of 4.2 g of 2-chloro-N4-(2,2-dimethyl-propyl)-pyrimidine-4,5-diamine in 40 ml of DMA was added 1.6 ml of POCl3. The solution was stirred at 100° C. for 2 hours, cooled and extracted with ethyl acetate and saturated NaHCO3 solution. The organic phases were dried over sodium sulfate and evaporated to dryness yielding 2-chloro-9-(2,2-dimethyl-propyl)-8-methyl-9H-purine as a brown oil.

Workup

temperaturecooled
extractionextracted with ethyl acetate and saturated NaHCO3 solution
dry with materialThe organic phases were dried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-b5863ba0d3594366bba27b279bff0551
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452886B2

Reaction notes

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