三乙胺 → Methyl 2-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate

HRID 515953

反应方程式

HRID 515953 反应方程式
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:4]([NH:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[N:3]=1.[NH2:21][C@@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]1[NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32].C(N(CC)CC)C>CC(N(C)C)=O.CCOC(C)=O>[C:31]([O:30][C:29]([NH:28][C@H:23]1[CH2:24][CH2:25][CH2:26][CH2:27][C@H:22]1[NH:21][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:4]([NH:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[N:3]=1)=[O:35])([CH3:34])([CH3:32])[CH3:33]

参与物

6

反应物 3

HCID 8471三乙胺HCID 15143891-N-叔丁氧羰基-1,2-顺式环己二胺HCID 58317549Methyl 2-chloro-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate

产物 1

HCID 67238015Methyl 2-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate收率 62.2%

试剂、催化剂与溶剂 2

HCID 8857乙酸乙酯溶剂HCID 31374N,N-二甲基乙酰胺溶剂

实验过程

A solution of methyl 2-chloro-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate (1.2 g, 4.11 mmol), tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (0.882 g, 4.11 mmol) and triethylamine (1.720 mL, 12.34 mmol) in DMA (10 mL) was heated at 90° C. for 4 h. The solution was then diluted with EtOAc, washed with brine and water. The organic extract was dried and concentrated under reduced pressure to give a light yellow residue; white crystals were formed upon triturating with ACN (5 mL). The resultant solid was filtered, washed with ACN, and dried to give the title compound as white solid (1.2 g, 62%). [M+H] calc'd for C25H35N5O4, 470; found, 470.

后处理

  1. washwashed with brine and water
  2. extractionThe organic extract
  3. customwas dried
  4. concentrationconcentrated under reduced pressure
  5. customto give a light yellow residue
  6. customwhite crystals were formed
  7. customupon triturating with ACN (5 mL)
  8. filtrationThe resultant solid was filtered
  9. washwashed with ACN
  10. customdried

来源与证据

ORD记录
ord-805520152a0b406485e703eae335253d
来源数据集
uspto-grants-2015_08
专利号
US09108970B2

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