HCID 66678959, compound → (S)-4-(6-chloro-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholine

HRID 1771572Notes

Reaction equation

HRID 1771572 reaction equation
FC1C=C([C:8]2[N:13]=[C:12]([S:14][CH3:15])[N:11]=[C:10]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]3[CH3:22])[CH:9]=2)C=NC=1.[Cl:23]C1N=C(N2CCOC[C@@H]2C)C=C(C2C=NC=C(F)C=2)N=1.FC1C=C(NC(NCCO)=O)C=CC=1B1OC(C)(C)C(C)(C)O1>>[Cl:23][C:8]1[N:13]=[C:12]([S:14][CH3:15])[N:11]=[C:10]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]2[CH3:22])[CH:9]=1

Participants

4

Reactant 3

HCID 66678959HCID 66678959, compound2×HCID 67382782(S)-4-(6-(5-fluoropyridin-3-yl)-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholineHCID 86691143(S)-4-(2-chloro-6-(5-fluoropyridin-3-yl)pyrimidin-4-yl)-3-methylmorpholine2×

Product 1

HCID 86691142(S)-4-(6-chloro-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholineYield 25%

Procedure

Method as described for intermediate 5 using (S)-4-(2-chloro-6-(5-fluoropyridin-3-yl)pyrimidin-4-yl)-3-methylmorpholine (intermediate 7) and 1-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(2-hydroxyethyl)urea (intermediate 13). Material was purified by prep HPLC (high pH) to afford a brown solid, (4 1 mg, 25%).

Workup

  1. customMaterial was purified by prep HPLC (high pH)

Sources & evidence

ORD record
ord-1ba09c1fcccc47da9453e5ccca97a784
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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