Benzyl Alcohol → HCID 131724598, compound

HRID 1007755Notes

Reaction equation

HRID 1007755 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C(OC([NH:18][C@H:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]1[NH:25][C:26]1[N:31]=[C:30]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=2)[C:29]([C:40]#N)=[C:28](Cl)[N:27]=1)=O)(C)(C)C.C[N:44]([CH:46]=[O:47])C>>[NH2:18][C@H:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]1[NH:25][C:26]1[N:27]=[C:28]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:29]([CH2:40][C:46]([NH2:44])=[O:47])=[C:30]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=2)[N:31]=1

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 86759532HCID 86759532, compound

Product 1

HCID 131724598HCID 131724598, compound

Conditions

Temperature
60 °C

Procedure

To a mixture of benzyl alcohol and DMF was added 60% sodium hydride under ice cooling and then 2-[cis-2-(tert-butoxycarbonylamino)cyclohexylamino]-6-chloro-4-(3-methylanilino)pyrimidine-5-carbonitrile was added thereto, followed by stirring at 60° C. for 40 minutes. Then, distilled water was added to the reaction liquid and the resulting precipitate was collected by filtration. The filtration product was treated in a similar manner to Reference Example 4 to obtain 2-(cis-2-aminocyclohexylamino)-4-benzyloxy-6-(3-methylanilino)pyrimidine-5-carboxyamide (colorless solid).

Workup

  1. distillationThen, distilled water
  2. additionwas added to the reaction liquid
  3. filtrationthe resulting precipitate was collected by filtration
  4. additionThe filtration product was treated in a similar manner to Reference Example 4

Sources & evidence

ORD record
ord-e138726bb8b54ba088ff5e3800438824
Source dataset
uspto-grants-2004_09
Patent number
US06797706B1

Reaction notes

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