Ethyl orthoformate → HCID 178482080, compound

HRID 527937Notes

Reaction equation

HRID 527937 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:24])[C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([NH2:23])[N:17]=3)[CH2:11]2)=[N:3][CH:2]=1.[CH2:25](OC(OCC)OCC)C.O.CC1C=CC(S(O)(=O)=O)=CC=1>CO>[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:24])[C:16]3[N:17]=[C:18]4[NH:23][CH:25]=[N:22][C:19]4=[CH:20][CH:21]=3)[CH2:11]2)=[N:3][CH:2]=1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 68027261HCID 68027261, compound

Product 1

HCID 178482080HCID 178482080, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (R)—N2-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-N2-methylpyridine-2,5,6-triamine (35 mg, 0.11 mmol), triethoxymethane (0.58 mL, 3.45 mmol) and 4-methylbenzenesulfonic acid monohydrate (62 mg, 0.33 mmol) in methanol (3.0 mL) was stirred at 150° C. for 5 min in an Initator™ Biotage microwave reactor. The volatiles were removed and the residue is purified by chromatography to give the title product. MS (m/z): 335 (M+H)+.

Workup

  1. customThe volatiles were removed
  2. customthe residue is purified by chromatography

Sources & evidence

ORD record
ord-2ef97ca8b1584e8b9cb5c7f1c374be32
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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