Methanol → HCID 88485499, compound

HRID 1591417Notes

Reaction equation

HRID 1591417 reaction equation
Cl[C:2]1[C:7]([NH:8][CH:9]=[O:10])=[C:6]([Cl:11])[N:5]=[C:4]([NH:12][C:13](=[O:15])[CH3:14])[N:3]=1.C(N(CC)CC)C.ClC1C(NC=O)=C([NH:33][C@H:34]2[CH2:38][C@@H:37]([CH2:39][OH:40])[CH:36]=[CH:35]2)N=C(NC(=O)C)N=1.CO>C(O)C>[Cl:11][C@H:6]1[C:7]([NH:8][CH:9]=[O:10])([NH:33][C@@H:34]2[CH2:38][C@H:37]([CH2:39][OH:40])[CH:36]=[CH:35]2)[CH:2]=[N:3][C:4]([NH:12][C:13](=[O:15])[CH3:14])=[N:5]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 16638380HCID 16638380, compoundHCID 86745456HCID 86745456, compound

Product 1

HCID 88485499HCID 88485499, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(1S,4R)-4-Amino-2-cyclopentene-1-methanol dibenzoyl-D-tartrate prepared as described in Example 13 (2.76 g, 9.02 mmol) was dissolved in water (20 mL) and applied to a column of 65 mL of Amberlite IA-400 (OH- form) anion exchange resin. The column was washed with water. Basic fractions were combined and evaporated to a residual oil which was dried by evaporation of absolute ethanol and then at 0.5 mm to give (1S,4R)-4-amino-2-cyclopentene-1-methanol (1.2 g) as a pale yellow oil (darkens rapidly in air) which was used immediately. This oil was dissolved in ethanol (5 mL) and added to a solution of N-(4,6-dichloro-5-formamido-2-pyrimidinyl)acetamide (2.07 g, 8.31 mmol), prepared as described in Example 15, and triethylamine (2.50 g, 24.8 mmol). The resulting dark solution was heated (oil bath 75°-80° C.) under nitrogen for 50 minutes. The solution was evaporated to a syrup which was applied to a silica gel column. Title compound was eluted with 3 to 5% methanol-chloroform as a pale yellow solid foam (1.59 g, 54%); 1H-NMR identical with that of crystallized sample. Such a sample was crystallized from ethanol to give white granules, m.p. 194°-195° C.; 1H-NMR (DMSO-d6) identical with that of the title compound of Example 15; [α]D20 +2.7°, [α]578 ° +3.6°, [α]54620 +2.9°, [α]43620 -2.5°, [α]36520 -41.2° (c=0.238, methanol).

Workup

  1. customprepared
  2. temperatureThe resulting dark solution was heated (oil bath 75°-80° C.) under nitrogen for 50 minutes
  3. customThe solution was evaporated to a syrup which
  4. washTitle compound was eluted with 3 to 5% methanol-chloroform as a pale yellow solid foam (1.59 g, 54%)
  5. customSuch a sample was crystallized from ethanol
  6. customto give white granules, m.p. 194°-195° C.

Sources & evidence

ORD record
ord-2589df5546e44cc493fff3440c7cabc3
Source dataset
uspto-grants-1993_04
Patent number
US05206435

Reaction notes

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