Methane → HCID 178525289, compound

HRID 2304829Notes

Reaction equation

HRID 2304829 reaction equation
C([O:3][C:4](=[O:40])[CH:5](Br)[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:15][C:16]3[N:17]([CH2:32][CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)[C:18](=[O:31])[N:19]([CH2:24][CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[C:20](=[O:23])[C:21]=3[N:22]=2)=[CH:10][CH:9]=1)Br)C.CC(C)([O-])C.[K+].C>C(O)(C)(C)C.O>[CH:25]1([CH2:24][N:19]2[C:20](=[O:23])[C:21]3[N:22]=[C:14]([C:11]4[CH:10]=[CH:9][C:8]([C:6]#[C:5][C:4]([OH:40])=[O:3])=[CH:13][CH:12]=4)[NH:15][C:16]=3[N:17]([CH2:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)[C:18]2=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

6

Reactant 3

HCID 297MethaneHCID 23665647Potassium tert-butoxideHCID 178470568HCID 178470568, compound

Product 1

HCID 178525289HCID 178525289, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

2.8 g (4.1 mmol) 3-[4-[1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl]phenyl}-2,3-dibromo-propionic acid ethyl ester (part a of this example) was added to 56 mL of 1M potassium t-butoxide in t-butanol (Aldrich) at room temperature. The mixture was stirred at room temperature for 2.5 hours, then 0.10 mL water was added. The solution was stirred for an additional hour then 1 g charcoal was added in 250 mL water. The mixture was stirred for 30 minutes then filtered. The filtrate was acidified with conc. hydrochloric acid (pH=1), then the resulting suspension was stirred for 15 minutes, filtered then washed with 3×50 mL water. The solid was dried under reduced pressure to give 1.63 g (81%) of title compound; 1H-NMR (DMSO-d6)δ: 8.15 (d, J=8.0 Hz, phenyl CH, 2H), 7.73 (d, J=8.0 Hz, phenyl CH, 2H), 3.87 (d, J=6.6 Hz, CH2N, 2H), 3.74 (d, J=6.8 Hz, CH2N, 2H), 1.88 (br s, c-hexyl CH, 1H), 1.4-1.8 (m, c-hexyl CH, CH2, 11H), 0.8-1.2 (m, c-hexyl CH2, 10 H); MS (ES−): 487 (M-1), 443 (M-1-CO2).

Workup

  1. stirringThe solution was stirred for an additional hour
  2. stirringThe mixture was stirred for 30 minutes
  3. filtrationthen filtered
  4. stirringthe resulting suspension was stirred for 15 minutes
  5. filtrationfiltered
  6. washthen washed with 3×50 mL water
  7. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-94b0faaf63ef46199d22553d73ca6b6c
Source dataset
uspto-grants-2002_08
Patent number
US06437124B1

Reaction notes

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