Triethylamine → 4'-(cyclopropylmethyl)-N2-(tetrahydro-2H-pyran-3-yl)-4,5'-bipyrimidine-2,2'-diamine

HRID 1397144Notes

Reaction equation

HRID 1397144 reaction equation
[CH:1]1([CH2:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13](S(C)=O)[N:12]=3)=[CH:9][N:8]=[C:7]([NH2:20])[N:6]=2)[CH2:3][CH2:2]1.Cl.[O:22]1[CH2:27][CH2:26][CH2:25][CH:24]([NH2:28])[CH2:23]1.C(N(CC)CC)C>CS(C)=O>[CH:1]1([CH2:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:28][CH:24]4[CH2:25][CH2:26][CH2:27][O:22][CH2:23]4)[N:12]=3)=[CH:9][N:8]=[C:7]([NH2:20])[N:6]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 46735995Oxan-3-amine hydrochlorideHCID 679839214'-(Cyclopropylmethyl)-2-(methylsulfinyl)-4,5'-bipyrimidin-2'-amine

Product 1

HCID 679834404'-(cyclopropylmethyl)-N2-(tetrahydro-2H-pyran-3-yl)-4,5'-bipyrimidine-2,2'-diamineYield 13%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4′-(cyclopropylmethyl)-2-(methylsulfinyl)-4,5′-bipyrimidin-2′-amine (5-2) (50 mg, 0.173 mmol) in DMSO (1 ml), was added Tetrahydro-pyran-3-ylamine HCl (119 mg, 0.864 mmol) and triethylamine (0.120 ml, 0.864 mmol) and the reaction was microwaved for 45 min at 160° C. The reaction was purified directly by reverse phase HPLC with a gradient of 10-90% acetonitrile in water over 15 minutes and then further purified by flash chromatography with a gradient of 25-100% ethyl acetate in heptane to give the desired product as a white solid (7.36 mg).

Workup

  1. customthe reaction was microwaved for 45 min at 160° C
  2. customThe reaction was purified directly by reverse phase HPLC with a gradient of 10-90% acetonitrile in water over 15 minutes
  3. customfurther purified by flash chromatography with a gradient of 25-100% ethyl acetate in heptane

Sources & evidence

ORD record
ord-a110978972a0424292e0429455a8b695
Source dataset
uspto-grants-2014_12
Patent number
US08901147B2

Reaction notes

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