Triethylamine → N-(3-amino-2,2-dimethylpropyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 2281437Notes

Reaction equation

HRID 2281437 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[CH3:12][C:13]([CH3:18])([CH2:16][NH2:17])[CH2:14][NH2:15].C(N(CC)CC)C>C(O)CCC>[NH2:15][CH2:14][C:13]([CH3:18])([CH3:12])[CH2:16][NH:17][C:4]1[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=[C:2]([Cl:1])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 817702,2-Dimethyl-1,3-propanediamineHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 86636615N-(3-amino-2,2-dimethylpropyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 92.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

To 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (170 mg, 0.904 mmol) in solid form in a round-bottom flask, a solution of 2,2-dimethyl-1,3-propanediamine (0.325 mL, 2.71 mmol) and triethylamine (0.150 mL, 1.08 mmol) in nBuOH (4 mL) was added. The mixture was heated at 70° C. for 3 h. It was then purified by HPLC to give N-(3-amino-2,2-dimethylpropyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-amine as a solid (212 mg).

Workup

  1. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-5725f552723f4243825cf960a40c22ec
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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