Ammonia → HCID 178513788, compound

HRID 391692Notes

Reaction equation

HRID 391692 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 178496597HCID 178496597, compoundHCID 178499069HCID 178499069, compound

Product 1

HCID 178513788HCID 178513788, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

9-(trans-4-Methoxycyclohexyl)-2-(3-hydroxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide. Methyl 9-(trans-4-methoxycyclohexyl)-8-oxo-2-(3-(triisopropylsilyloxy)phenyl)-8,9-dihydro-7H-purine-6-carboxylate (0.205 g, 370 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 resulting 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, 66%). 1H NMR (400 MHz, DMSO-d6) δ 11.51 (s, 1H), 9.55 (s, 1H), 8.33 (s, 1H), 8.01 (d, J=7.59, 1H), 7.91 (s, 1H), 7.89 (s, 1H), 7.29 (t, J=7.99, 1H), 6.7 (dd, J=7.59, 1.59, 1H), 4.27 (m, 1H), 3.34 (s, 3H), 3.31 (s, 1H), 2.18 (d, J=10.79, 2H), 1.82 (d, J=11.19, 2H), 1.31 (q, J=12.39, 2H); MS (ESI) m/z 384.4 [M+1]+; mp 355-357° C.

Workup

  1. customcondensed under reduced pressure
  2. additionwas added
  3. filtrationAfter two h, the resulting 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-407b7e82e84c427a8df9c97bdde29641
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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