Triethylamine → HCID 11994302, compound

HRID 986924Notes

Reaction equation

HRID 986924 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:7][C@H:6]([CH2:8][OH:9])[CH:5]=[CH:4]1.OC[C@@H]1C[C@H](NC(=O)OC(C)(C)C)C=C1.[NH2:25][C:26]1[C:27]([Cl:33])=[N:28][CH:29]=[N:30][C:31]=1Cl.C(N(CC)CC)C.[OH-].[Na+]>C(O)CCC>[NH2:25][C:26]1[C:31]([NH:2][C@H:3]2[CH2:7][C@@H:6]([CH2:8][OH:9])[CH:5]=[CH:4]2)=[N:30][CH:29]=[N:28][C:27]=1[Cl:33]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 794345-Amino-4,6-dichloropyrimidineHCID 18453470HCID 18453470, compoundHCID 534718602-Cyclopentene-1-methanol, 4-amino-, hydrochloride (1:1), (1S,4R)-

Product 1

HCID 11994302HCID 11994302, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (+)-(1S,4R)-4-amino-2-cyclopentene-1-methanol hydrochloride (from deblocking of 10.66 g, 50.0 mmoles of (+)-(1S,4R)-tert-butyl N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]carbamate as described in part c of this example), 5-amino-4,6-dichloropyrimidine (Aldrich, 16.40 g, 0.100 mole), and triethylamine (15.2 g, 0.150 mole) in 1-butanol (25 mL) was refluxed under nitrogen for 18 hours. The solution was cooled and 1 N sodium hydroxide (100 mL) added. Volatiles were evaporated under reduced pressure and the residual solid was chromatographed on silica gel. Title compound eluted with 5% methanol-chloroform as a pale yellow glass (10.8 g). Crystallization of such a sample from ethyl acetate gave title compound as white needles, m.p. 151-154° C.; 1H-NMR (DMSO-d6) δ: 7.75 (s, 1H), 6.76 (d, J=6.8 Hz, 1H), 5.93 and 5.82 (two m, 2H), 5.11 (m, 3H), 4.66 (t, J=5.3 Hz, 1H), 3.40 (br t, J=6.1 Hz, 2H), 2.75 (m, 1H), 2.20 (m, 1H), 1.38 (m, 1H).

Workup

  1. temperaturewas refluxed under nitrogen for 18 hours
  2. temperatureThe solution was cooled
  3. customVolatiles were evaporated under reduced pressure
  4. customthe residual solid was chromatographed on silica gel
  5. washTitle compound eluted with 5% methanol-chloroform as a pale yellow glass (10.8 g)
  6. customCrystallization of such a sample from ethyl acetate

Sources & evidence

ORD record
ord-fae623ba847542ec857e9dbb43dcf76a
Source dataset
uspto-grants-2003_10
Patent number
US06630477B1

Reaction notes

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