Hydrochloric Acid → 8-chloro-3-(3-methylbutyl)-3,7-dihydro-1H-purine-2,6-dione

HRID 2386614Notes

Reaction equation

HRID 2386614 reaction equation
[Cl:1][C:2]1[N:10](CC=C)[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[C:4]=2[N:3]=1.N1CCOCC1.Cl.C(OCC)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[C:4]=2[N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8083MorpholineHCID 592995788-chloro-3-(3-methylbutyl)-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 592995308-chloro-3-(3-methylbutyl)-3,7-dihydro-1H-purine-2,6-dioneYield 56.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8-chloro-3-(3-methylbutyl)-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (0.074 g, 0.25 mmol) in THF (2 ml) was treated with morpholine (0.035 ml, 4.0 mmol) and the mixture degassed by the repeated alternate application of vacuum and nitrogen to the reaction vessel. The mixture was then treated with a solution of tetrakis(triphenylphosphine)palladium(0) (0.03 g, 0.026 mmol) in degassed THF (0.5 ml). After 2 hours the mixture was treated with 2M aqueous hydrochloric acid (2 ml) and diethyl ether (3 ml). The precipitated product was filtered off, washed with diethyl ether and dried. This yielded the title compound as a white solid (0.036 g, 56%). NMR δH (400 MHz, d6-DMSO); 0.91 (d, 6H, J=6.3 Hz), 1.47-1.62 (m, 3H), 3.87 (t, 2H, J=7.5 Hz), 11.19 (br. s, 1H), 14.38 (br. s, 1H); m/z 257, 259 [MH+].

Workup

  1. customthe mixture degassed by the repeated alternate application of vacuum and nitrogen to the reaction vessel
  2. filtrationThe precipitated product was filtered off
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-10d2ccdee6e54f9f8cee7b2b255931c0
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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