Water → HCID 86680733, compound

HRID 1910450Notes

Reaction equation

HRID 1910450 reaction equation
[NH2:1][CH2:2][C:3]1([NH2:7])[CH2:6][O:5][CH2:4]1.C(N(CC)CC)C.[Cl:15][C:16]1[N:17]=[C:18](Cl)[C:19]2[S:24][CH:23]=[CH:22][C:20]=2[N:21]=1.O>ClCCl>[NH2:7][C:3]1([CH2:2][NH:1][C:18]2[C:19]3[S:24][CH:23]=[CH:22][C:20]=3[N:21]=[C:16]([Cl:15])[N:17]=2)[CH2:6][O:5][CH2:4]1.[NH2:1][CH2:2][C:3]1([NH:7][C:18]2[C:19]3[S:24][CH:23]=[CH:22][C:20]=3[N:21]=[C:16]([Cl:15])[N:17]=2)[CH2:6][O:5][CH2:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 127128322,4-Dichlorothieno[3,2-d]pyrimidineHCID 217130163-(Aminomethyl)oxetan-3-amine

Product 2

HCID 86680733HCID 86680733, compoundYield 153.9%HCID 86680734HCID 86680734, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-aminomethyloxetan-3-ylamine (0.98 g, 9.6 mmol) in dichloromethane (15 mL) and triethylamine (4 mL, 28.7 mol) was added a solution of 2,4-dichlorothieno[3,2-d]pyrimidine (1.0 g, 4.8 mmol) dropwise in dichloromethane (5 mL). The mixture was stirred at room temperature overnight, then water (50 mL) was added. The mixture was extracted with dichloromethane. The organic phase was washed with brine, dried with anhydrous sodium sulfate. The solvent was then removed and the residue was purified by flash column chromatography (eluting with 10%˜30% methanol in dichloromethane) to give 1.0 g of N-[(3-aminooxetan-3-yl)methyl]-2-chlorothieno[3,2-d]pyrimidin-4-amine and N-[3-(aminomethyl)oxetan-3-yl]-2-chlorothieno[3,2-d]pyrimidin-4-amine (yield was 77%). MS obsd. (ESI+) [(M+H)+] 271.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washThe organic phase was washed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was then removed
  5. customthe residue was purified by flash column chromatography (eluting with 10%˜30% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c8096584659048e4940e10edc2cb5672
Source dataset
uspto-grants-2013_12
Patent number
US08604019B2

Reaction notes

Loading…