Ammonia → HCID 178508629, compound

HRID 1028770Notes

Reaction equation

HRID 1028770 reaction equation
[NH3:1].Cl[C:3]1[C:4]2[C:11]([I:12])=[CH:10][N:9]([C@H:13]3[CH2:16][C@H:15]([CH2:17][OH:18])[CH2:14]3)[C:5]=2[N:6]=[CH:7][N:8]=1.C(=O)=O.CC(C)=O>O1CCOCC1.CC(O)C>[NH2:1][C:3]1[C:4]2[C:11]([I:12])=[CH:10][N:9]([C@H:13]3[CH2:16][C@H:15]([CH2:17][OH:18])[CH2:14]3)[C:5]=2[N:6]=[CH:7][N:8]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 18522661Acetone cardiceHCID 178521038HCID 178521038, compound

Product 1

HCID 178508629HCID 178508629, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Gaseous ammonia (from a lecture bottle) was condensed into a suspension of trans-[3-(4-chloro-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutyl]-methanol (172.6 mg, 0.475 mmol) in dioxane (3 mL) and iPrOH (3 mL) in a sealable glass tube, cooled by dry ice/acetone, until the volume increased by mL, then the tube was sealed and heated to 90° C. overnight. The solvents were evaporated, water was added to the residue, and the pale yellow solid was filtered off and dried in vacuo to give the title compound as a pale yellow solid. The compound was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 2.41-2.52 (m, 2H), 2.52-2.64 (m, 3H), 3.83 (d, 0.1=6.3 Hz, 2H), 5.30-5.40 (mc, 1H), 5.60 (brs, 2H), 7.29 (s, 1H), 8.26 (s, 1H). MS (ES+): m/z 345.1 (100) [MH+]. HPLC: tR=1.9 min (OpenLynx, polar—5 min).

Workup

  1. customcondensed
  2. temperatureincreased by mL
  3. customthe tube was sealed
  4. customThe solvents were evaporated
  5. additionwater was added to the residue
  6. filtrationthe pale yellow solid was filtered off
  7. customdried in vacuo

Sources & evidence

ORD record
ord-0a8e17f2fe8e4f5cbfc5be55f3be0a62
Source dataset
uspto-grants-2014_05
Patent number
US08735405B2

Reaction notes

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