Water → HCID 178448887, compound

HRID 2201984Notes

Reaction equation

HRID 2201984 reaction equation
[C:1]([NH:5][C:6]1[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=[C:8](Cl)[N:7]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20][CH2:19]1.C([O-])([O-])=O.[Na+].[Na+].O>CN1C(=O)CCC1>[C:1]([NH:5][C:6]1[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=[C:8]([NH:17][C@H:18]2[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20][CH2:19]2)[N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 118253787HCID 118253787, compoundHCID 178479278HCID 178479278, compound

Product 1

HCID 178448887HCID 178448887, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-(tert-butylamino)-2-chloropyrimidine-5-carboxamide (0.5 g), trans-4-aminocyclohexanol hydrochloride (0.40 g), Na2CO3 (0.28 g) in NMP (3.5 mL) was heated at 85° C. and held for 6 h. The mixture was cooled to 35° C., and water (10 mL) was added. After 30 minutes, the batch was cooled to 25° C. and held for 1 h. The suspension was filtered, washed with water (2.5 mL) and dried in a vacuum oven at 40° C. with a nitrogen bleed for 24 h to give 4-(tert-butylamino)-2-((trans-4-hydroxycyclohexyl)amino)pyrimidine-5-carboxamide as a white solid (0.6 g, 89%). 1H NMR (DMSO-d6) δ 9.17 (broads, 1H), 8.32 (s, 1H), 7.01 (broads, 1H), 4.52 (d, J=4.5 Hz, 1H), 3.70-3.25 (m, 2H), 1.84 (m, 4H), 1.41 (s, 9H), 1.33-1.16 (m, 4H).

Workup

  1. temperatureThe mixture was cooled to 35° C.
  2. waitAfter 30 minutes
  3. temperaturethe batch was cooled to 25° C.
  4. waitheld for 1 h
  5. filtrationThe suspension was filtered
  6. washwashed with water (2.5 mL)
  7. customdried in a vacuum oven at 40° C. with a nitrogen
  8. waitbleed for 24 h

Sources & evidence

ORD record
ord-07befe0770984d00bd84ca79755b7ef7
Source dataset
uspto-grants-2016_06
Patent number
US09365524B2

Reaction notes

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