2-Amino-4-chloro-6-methylpyrimidine → HCID 71270199, compound

HRID 1626922Notes

Reaction equation

HRID 1626922 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH2:10][C@H:11]([C:13]1[N:14]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:15](=[O:24])[C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])[CH3:12].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH:10][C@H:11]([C:13]2[N:14]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:15](=[O:24])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:23])[CH3:12])[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 81531DiisopropylethylamineHCID 66607319(S)-3-(1-aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one

Product 1

HCID 71270199HCID 71270199, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

To a stirred mixture of 2-amino-4-chloro-6-methylpyrimidine (0.266 mmol, 1.62 eq) and compound 1 (0.164 mmol, 0.164 mmol, 1 eq) in NMP (1.5 ml), DIPEA (0.656 mmol, 4 eq) was added. The mixture was heated to 160° C. for 12 hours. Then the mixture was extracted with ethyl acetate and washed with water and brine. The product was purified by silica gel column chromatography eluting with DCM/methanol (from 0 to 10%) to afford the product (S)-3-(1-((2-amino-6-methylpyrimidin-4-yl)amino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one 92. ESI-MS m/z: 406.2 [M+H]+.

Workup

  1. additionwas added
  2. extractionThen the mixture was extracted with ethyl acetate
  3. washwashed with water and brine
  4. customThe product was purified by silica gel column chromatography
  5. washeluting with DCM/methanol (from 0 to 10%)

Sources & evidence

ORD record
ord-14c3754cd5bc44ab9d7eb8e81523b178
Source dataset
uspto-grants-2014_07
Patent number
US08785470B2

Reaction notes

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