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1-Butanol → HCID 57990349, compound

HRID 2281516
Notes
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Reaction equation

HRID 2281516 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([I:11])=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C.C(O)CCC>O1CCOCC1.CN(C=O)C>[CH2:23]([NH:30][C:4]1[C:5]2[C:10]([I:11])=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=[C:2]([Cl:1])[N:3]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 2631-ButanolHCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 579902932,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 57990349HCID 57990349, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (1.00 g, 2.13 mmol), benzylamine (0.233 mL, 2.13 mmol) and DIEA (0.750 mL, 4.31 mmol) in dioxane (12 mL)/nBuOH (12 mL)/DMF (3 mL) was stirred at 70° C. for 2 h. It was concentrated in vacuo. The residue was partitioned between water and EtOAc. The organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give N-benzyl-2-chloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.993 g).

Workup

  1. concentrationIt was concentrated in vacuo
  2. customThe residue was partitioned between water and EtOAc
  3. customThe organic phase was separated
  4. washwashed with 1N HCl
  5. dry with materialwith 5% NaHCO3, dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc8e306b9cd145268a0eca75da9c97fc
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09139581B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes