Ammonia → HCID 178513787, compound

HRID 391694Notes

Reaction equation

HRID 391694 reaction equation
C[O:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]2[C:17](=[O:18])[NH:16][C:15]3[C:10]2=[N:11][C:12]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=2)=[N:13][C:14]=3[C:19]([NH2:21])=[O:20])[CH2:5][CH2:4]1.CO[C@@H]1CC[C@H](N2C(=O)NC3C2=NC(C2C=CC=C(O[Si](C(C)C)(C(C)C)C(C)C)C=2)=NC=3C(OC)=O)CC1.N>CO.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]2[C:17](=[O:18])[NH:16][C:15]3[C:10]2=[N:11][C:12]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=2)=[N:13][C:14]=3[C:19]([NH2:21])=[O:20])[CH2:5][CH2:4]1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 178496596HCID 178496596, compoundHCID 178499068HCID 178499068, compound

Product 1

HCID 178513787HCID 178513787, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

9-(cis-4-Methoxycyclohexyl)-2-(3-hydroxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide. Methyl 9-(cis-4-methoxycyclohexyl)-8-oxo-2-(3-(triisopropylsilyloxy)phenyl)-8,9-dihydro-7H-purine-6-carboxylate (0.210 g, 377 mmol) was dissolved in methanol (15 mL) reacted with ammonia gas according to General Procedure G. After 16 h, the solution was condensed under reduced pressure and the resultant crude product diluted with tetrahydrofuran (15 mL) and 1.0M tetrabutylammonium fluoride in tetrahydrofuran (0.92 mL) was added. After two h, the resultant precipitate was filtered and washed with tetrahydrofuran followed by hexanes. The product was purified using reverse-phase preparative HPLC (20 to 100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min) to afford the title compound (0.093 g, 64%). 1H NMR (400 MHz, DMSO-d6) δ 11.48 (s, 1H), 9.47 (s, 1H), 8.32 (s, 1H), 8.03 (d, J=7.59, 1H), 7.92 (s, 2H), 7.28 (t, J=7.59, 1H), 6.86 (dd, J=7.99, 2.39, 1H), 4.30 (m, 1H), 3.49 (s, 1H), 3.34 (s, 3H), 2.71 (m, 2H), 2.06 (s, 1H), 2.03 (s, 1H), 1.53 (m, 4H); MS (ESI) m/z 384.4. [M+1]+; mp 345-347° C.

Workup

  1. customcondensed under reduced pressure
  2. additionwas added
  3. filtrationAfter two h, the resultant precipitate was filtered
  4. washwashed with tetrahydrofuran
  5. customThe product was purified
  6. customreverse-phase preparative HPLC (20 to 100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min)

Sources & evidence

ORD record
ord-e2584e92978e4d879fa9a2f62b1dc29d
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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