4-Amino-6-chloropyrimidine → HCID 86686852, compound

HRID 402955Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[Cl:16][C:17]1[N:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=1.CN(C1C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=CC=1)C.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:16][C:17]1[N:22]=[CH:21][N:20]=[C:19]([NH:23][C:2]2[N:7]=[CH:6][C:5]([C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[O:9])=[CH:4][CH:3]=2)[CH:18]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a stirred solution of (6-bromopyridin-3-yl)(morpholino)methanone (0.75 g, 2.78 mmol) in toluene (5 mL) was added 6-chloropyrimidin-4-amine (0.43 g, 3.33 mmol), Pd2(dba)3 (100 mg, 0.3 mmol), Davephos (157 mg, 0.4 mmol) and NaOt-Bu (848 mg, 8 mmol). The mixture was stirred at 150° C. for 13 hrs under N2. The mixture was evaporated and the residue was taken up in ethyl acetate (50 mL) and H2O (20 mL). The organic phase was washed with H2O (2×20 mL) and then brine (2×20 mL) and dried over Na2SO4. After filtration and concentration, the final product (350 mg, 40%) was obtained as yellow solid. LC-MS: 320.1 [M+H]+, tR=1.306 min.

Workup

customThe mixture was evaporated
washThe organic phase was washed with H2O (2×20 mL)
dry with materialbrine (2×20 mL) and dried over Na2SO4
filtrationAfter filtration and concentration

Sources & evidence

ORD record: ord-8ecc71e327bd49ab9e1f105ee9f6ffa4
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742098B2

Reaction notes

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