Ammonia → HCID 178490818, compound

HRID 1976552Notes

Reaction equation

HRID 1976552 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[CH2:10][N:11]2[C:19]3[N:18]=[C:17]([CH:20]([CH3:22])[CH3:21])[NH:16][C:15]=3[C:14](=O)[N:13]=[CH:12]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)=O.ClC1N=C2C(NC=N2)=C[N:36]=1.N>C1COCC1>[NH2:36][C:14]1[N:13]=[CH:12][N:11]([CH2:10][C:9]2[CH:24]=[CH:25][C:26]([O:27][CH3:28])=[C:7]([O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:8]=2)[C:19]2[C:15]=1[N:16]=[C:17]([CH:20]([CH3:22])[CH3:21])[N:18]=2

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 24813Phosphorus oxychlorideHCID 5193142-chloro-7H-purineHCID 9800129HCID 9800129, compound

Product 1

HCID 178490818HCID 178490818, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(3-Cyclopentyloxy-4-methoxy-benzyl)-8-isopropyl-hypoxanthine (5.74 g, 15 mmole) and phosphorus oxychloride (60 ml) were heated to 65° C. for 30 minutes. The reaction mixture was evaporated to dryness in vacuo and the residue evaporated twice with toluene. The crude chloropurine (15 mmole) was dissolved in THF (80ml ) and 32% aqueous ammonia solution (36.2 ml) and heated together with liquid ammonia (50 g) in a 450 ml pressure reactor to 60° C. (340 psi) for 4 hours. The solvents were evaporated in vacuo and the residue suspended in a mixture of diethyl ether and 1 M NaOH solution. The solid was collected and crystallized from ethyl acetate to give the title compound, 3.92 g (68.5 %) mp 190-193° C.

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo
  2. customthe residue evaporated twice with toluene
  3. customThe solvents were evaporated in vacuo
  4. additionthe residue suspended in a mixture of diethyl ether and 1 M NaOH solution
  5. customThe solid was collected
  6. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-83cce36cb0c2470b810a27b0d8314f47
Source dataset
uspto-grants-2001_05
Patent number
US06228859B1

Reaction notes

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