Phenothiazine → 9-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]phenothiazine

HRID 1827712Notes

Reaction equation

HRID 1827712 reaction equation
NC1N=C(N)C2C(CN(C3C=CC=CC=3)C3C=CC=CC=3)=CSC=2N=1.[NH2:26][C:27]1[N:28]=[C:29]([NH2:37])[C:30]2[C:35]([CH3:36])=[CH:34][S:33][C:31]=2[N:32]=1.[CH:38]1[C:51]2[NH:50][C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[S:43][C:42]=2[CH:41]=[CH:40][CH:39]=1>>[NH2:26][C:27]1[N:28]=[C:29]([NH2:37])[C:30]2[C:35]([CH2:36][C:48]3[CH:47]=[CH:46][CH:45]=[C:44]4[C:49]=3[NH:50][C:51]3[CH:38]=[CH:39][CH:40]=[CH:41][C:42]=3[S:43]4)=[CH:34][S:33][C:31]=2[N:32]=1

Participants

4

Reactant 3

HCID 7108PhenothiazineHCID 9906281n-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-n,n-diphenylamineHCID 12659534Thieno[2,3-d]pyrimidine-2,4-diamine, 5-methyl-

Product 1

HCID 220630199-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]phenothiazine

Procedure

9-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]phenothiazine (Formula I: Ar=2,4-diaminothieno[2,3-d]pyrimidin-5-yl; W=CH2; X=N; Z=S; m=n=0) is prepared similarly to N-[(2,4-diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-N,N-diphenylamine as disclosed in Example 11 above by using 2,4-diamino-5-methylthieno[2,3-d]pyrimidine (1.3 g, 7.4 mmol) in Step 1 and phenothiazine (159 mg, 0.8 mmol) in Step 3. The final product and its intermediates can be purified by chromatography.

Workup

  1. customThe final product and its intermediates can be purified by chromatography

Sources & evidence

ORD record
ord-fe20ee7f059d456c93876ee6f0635ffe
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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