Dichloromethane → HCID 68294258, compound

HRID 2279483Notes

Reaction equation

HRID 2279483 reaction equation
[N:1]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[N:3][C:2]=1[NH:11][C@@H:12]([CH3:15])[CH2:13][OH:14].[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18].C(Cl)Cl>O>[Si:20]([O:14][CH2:13][C@@H:12]([NH:11][C:2]1[N:3]=[CH:4][C:5]2[CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[N:1]=1)[CH3:15])([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 68295199HCID 68295199, compound

Product 1

HCID 68294258HCID 68294258, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (S)-2-(5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-ylamino)propan-1-ol (138, 0.215 g, 1.03 mmol), TBDMS-Cl (0.171 g, 1.14 mmol) and TEA (0.216 ml, 1.55 mmol) and DCM (5 mL) were stirred for 18 h, poured into water and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered, and concentrated to give the crude product, which was purified by SiO2 chromatography eluting with DCM/MeOH (500:50) to afford 0.220 g (66.1%) of (S)—N-(1-(tert-butyldimethylsilyloxy)propan-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amine (152).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by SiO2 chromatography
  7. washeluting with DCM/MeOH (500:50)

Sources & evidence

ORD record
ord-00558d9d61ab444ca4d4b7355cf2c1ca
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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